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Dayang Chem (Hangzhou) Co.,Ltd.

Dayangchem's R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. DayangChem can provide different quantities

Reserpine Manufacturer/High quality/Best price/In stock

Cas:50-55-5

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Hebei yanxi chemical co.,LTD.

Hebei yanxi chemical co., LTD is a professional research, development and production 2-phenylacetamide enterprise backbone members by local well-known entrepreneurs and professional senior engineers in the party's "low carbon environ

Reserpine

Cas:50-55-5

Min.Order:100 Gram

FOB Price: $2.0

Type:Manufacturers

inquiry

Xi'an Quanao Biotech Co., Ltd.

Pharmaceutical Rauwolfia Extract 98% Reserpine powder Xi'an Quanao Biotech Co., Ltd. is is a global chemical industry manufacturers and suppliers of pharmaceuticals and intermediates, peptide,Nootropis etc API, food and feed additives, herbal

Pharmaceutical Rauwolfia Extract 98% Reserpine powder

Cas:50-55-5

Min.Order:100 Gram

FOB Price: $21.9 / 23.8

Type:Manufacturers

inquiry

Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

Factory Supply Reserpine

Cas:50-55-5

Min.Order:1

Negotiable

Type:Other

inquiry

Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

Shanghai Seasonsgreen Chemical Co.,Ltd

Shanghai Seasonsgreen Chemical is a high-tech research and development, production, sale and custom synthesis set in one high-tech chemical products enterprises. Our sales and marketing division is located in Shanghai, serving international pharmaceu

lower price High quality Reserpine

Cas:50-55-5

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Manufacturers

inquiry

Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

Reserpine (base and/or unspecified salts)

Cas:50-55-5

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Hubei DiBo chemical co., LTD

Name: Reserpine English Name: Reserpine CAS:50-55-5 Molecular formula: C33H40N2O9 Molecular weight: 608.69 Packaging Specification: 25kg/drum high purity 99%min stock Hubei DiBo Chemical Co., Ltd. was founded in 2009, is a high-tech indus

Reserpine material/CAS:50-55-5/Chinese suppliers

Cas:50-55-5

Min.Order:25 Kilogram

FOB Price: $1.0 / 2.0

Type:Other

inquiry

Kono Chem Co.,Ltd

Superiority pioneerbiotech is a leading manufacturer and supplier of chemicals in China. We develop ,produce and distribute high quality pharmaceuticals, intermediates, special chemicals and other fine chemicals. We could give you: 1.Best q

Reserpine

Cas:50-55-5

Min.Order:1 Gram

FOB Price: $800.0 / 1000.0

Type:Other

inquiry

Henan Tianfu Chemical Co., Ltd.

Our company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.O

high quality Reserpine

Cas:50-55-5

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Lab/Research institutions

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva

Reserpine

Cas:50-55-5

Min.Order:1 Gram

FOB Price: $12.0 / 15.0

Type:Trading Company

inquiry

Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

New production CAS 50-55-5 with best quality

Cas:50-55-5

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

inquiry

Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

Reserpine CAS NO.50-55-5

Cas:50-55-5

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

inquiry

Henan Sinotech Import&Export Corporation

Reserpine Product Description .Basic info.: Name: Reserpine Cas No.: 50-55-5 Apperance: White fine powder Purity: 8%,20%,40%,98%,4:1, 5:1 ,10:1

manufacturer supplier Reserpine 99% CAS 50-55-5

Cas:50-55-5

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Other

inquiry

Hangzhou Sartort Biopharma Co., Ltd

Appearance:off-white crystalline powder Storage:Room temperature Package:25kg/drum Application:Chemicals Transportation:Express/Sea/Air Port:Any port in china

High Quality Reserpine Factory Supply CAS:50-55-5

Cas:50-55-5

Min.Order:25 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hubei Langyou International Trading Co., Ltd

Our Adwantage: 1.We have stock so we can delivery quickly at the very day when receive the payment. 2.Best price, first class service, high successful delivery rate. A discount would be given when you make a large order. 3.High quality gua

Shanghai Upbio Tech Co.,Ltd

1,In No Less five years exporting experience. 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Onchem specialized in APIs, chemical intermed

Reserpine with high quality

Cas:50-55-5

Min.Order:100 Gram

FOB Price: $10.0

Type:Lab/Research institutions

inquiry

LIDE PHARMACEUTICALS LIMITED

Advantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the

Shanghai Minstar Chemical Co., Ltd

Reserpine Basic information Overview Indications Mode of action Adverse reactions Warning and precautions References Product Name: Reserpine CAS: 50-55-5 MF: C33H40N2O9 MW: 608.69 EINECS: 200-047-9 Mol File: 50-55-5.mol Reserpine

Reserpine

Cas:50-55-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Baoji Guokang Healthchem co.,ltd

Reserpine is an indole alkaloid, antipsychotic and antihypertensive drug that has been used for the control of high blood pressure and for the relief of psychotic symptoms. The antihypertensive actions of reserpine are a result of its ability to

Benazyl,Reserpine,cas:50-55-5

Cas:50-55-5

Min.Order:1 Gram

FOB Price: $11370.0 / 12120.0

Type:Trading Company

inquiry

Qingdao Beluga Import and Export Co., LTD

Reserpine CAS:50-55-5 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates, ste

Reserpine CAS:50-55-5

Cas:50-55-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

Lonwin Chemical Group Limited

Reserpine CAS: 50-55-5 Specification Item Standard Identification A.H-NMR:Comply with the structure B.LC-MS:Comply with the structure C.The IR spectrum of sample

Factory supply Reserpine

Cas:50-55-5

Min.Order:1 Kilogram

Negotiable

Type:Other

inquiry

Hebei Quanhe Biotechnology Co. LTD

1. Timely and efficient service to ensure communication with customers 2. Produce products of different specifications and sizes according to your requirements. 3. Quality procedures and standards recognized by SGS. Advanced plant equipment ensures s

Reserpine

Cas:50-55-5

Min.Order:1 Kilogram

FOB Price: $20.0 / 40.0

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

Triumph International Development Limilted

Appearance:white or light yellow crystalline powder Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for research and industrial manufacture. Transportation:By

Reserpine

Cas:50-55-5

Min.Order:100 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Afine Chemicals Limited

Our Services 1. New Molecules R&D 2. Own test center HPLC NMR GC LC-MS 3. API and Intermediates from China reputed manufacturers 4. Documents support COA MOA MSDS DMF open part Our advantages 1. Government awarded company. Top 100 enter

Reserpine

Cas:50-55-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Chengdu Biopurify Phytochemicals Ltd.

Chengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine,Traditional Chinese Medic

Reserpine

Cas:50-55-5

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Hubei Yuanmeng Biological Technology Co., Ltd.

Hubei Yuanmeng Biological Technology Co., Ltd., which is located in Wuhan, China. We are specializing in the exportation of APIs, and plant extracts ect. Our products has been exported to America, Australia, Brazil, the Europe, Middle East and other

High Purity Reserpine CAS 50-55-5 with Fast Shipment

Cas:50-55-5

Min.Order:1 Kilogram

FOB Price: $3.0 / 5.0

Type:Trading Company

inquiry

Hangzhou Keyingchem Co.,Ltd

Hangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det

Reserpine

Cas:50-55-5

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimb-3-enium; nitrate

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimb-3-enium; nitrate

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
With acetic acid; zinc
ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimb-3-enium; perchlorate

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimb-3-enium; perchlorate

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
With perchloric acid; zinc
Isoreserpin
482-85-9

Isoreserpin

A

reserpine
50-55-5

reserpine

B

C33H42N2O9
16625-52-8

C33H42N2O9

C

2,3-secoreserpine
16625-53-9

2,3-secoreserpine

Conditions
ConditionsYield
With acetic acid; zinc for 12h; Heating;A 195 mg
B 70 mg
C 22 mg
3,4,5-Trimethoxybenzoyl chloride
4521-61-3

3,4,5-Trimethoxybenzoyl chloride

methyl reserpate
2901-66-8

methyl reserpate

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane Ambient temperature; Yield given;
With pyridine at 20℃; for 96h;
(+-)-reserpine

(+-)-reserpine

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
With camphor-10-sulfonic acid
(1S,2R,3S,4S,7S)-3-(Fluoro-dimethyl-silanyl)-7-hydroxymethyl-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester
871938-44-2

(1S,2R,3S,4S,7S)-3-(Fluoro-dimethyl-silanyl)-7-hydroxymethyl-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: pyridine; 4-dimethylaminopyridine / CH2Cl2 / 10 h / Heating
2: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C
3: Ag2O; CaSO4 / 20 h
4: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
5: MgSO4 / acetonitrile / 1 h
6: aq. HCl / tetrahydrofuran / 30 h / 20 °C
7: pyridine / 96 h / 20 °C
View Scheme
(1R,5S,6S,7R,9S)-7-Methoxy-3-oxo-9-(toluene-4-sulfonyloxymethyl)-2-oxa-bicyclo[3.2.2]nonane-6-carboxylic acid methyl ester
871938-46-4

(1R,5S,6S,7R,9S)-7-Methoxy-3-oxo-9-(toluene-4-sulfonyloxymethyl)-2-oxa-bicyclo[3.2.2]nonane-6-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
2: MgSO4 / acetonitrile / 1 h
3: aq. HCl / tetrahydrofuran / 30 h / 20 °C
4: pyridine / 96 h / 20 °C
View Scheme
(1S,2R,3R,5S,6S)-3-Hydroxy-2-methoxy-6-(2-oxo-ethyl)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

(1S,2R,3R,5S,6S)-3-Hydroxy-2-methoxy-6-(2-oxo-ethyl)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: MgSO4 / acetonitrile / 1 h
2: aq. HCl / tetrahydrofuran / 30 h / 20 °C
3: pyridine / 96 h / 20 °C
View Scheme
(1R,5S,6S,7R,9S)-7-Hydroxy-3-oxo-9-(toluene-4-sulfonyloxymethyl)-2-oxa-bicyclo[3.2.2]nonane-6-carboxylic acid methyl ester

(1R,5S,6S,7R,9S)-7-Hydroxy-3-oxo-9-(toluene-4-sulfonyloxymethyl)-2-oxa-bicyclo[3.2.2]nonane-6-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Ag2O; CaSO4 / 20 h
2: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
3: MgSO4 / acetonitrile / 1 h
4: aq. HCl / tetrahydrofuran / 30 h / 20 °C
5: pyridine / 96 h / 20 °C
View Scheme
(1S,2R,3S,4S,7S)-7-Benzyloxymethyl-3-(fluoro-dimethyl-silanyl)-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

(1S,2R,3S,4S,7S)-7-Benzyloxymethyl-3-(fluoro-dimethyl-silanyl)-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: H2 / Pd/C / ethyl acetate / 30 h / 760 Torr
2: pyridine; 4-dimethylaminopyridine / CH2Cl2 / 10 h / Heating
3: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C
4: Ag2O; CaSO4 / 20 h
5: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
6: MgSO4 / acetonitrile / 1 h
7: aq. HCl / tetrahydrofuran / 30 h / 20 °C
8: pyridine / 96 h / 20 °C
View Scheme
(1S,2R,3S,4S,7S)-7-Benzyloxymethyl-3-(furan-2-yl-dimethyl-silanyl)-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester
871938-43-1

(1S,2R,3S,4S,7S)-7-Benzyloxymethyl-3-(furan-2-yl-dimethyl-silanyl)-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h / 20 °C
2: H2 / Pd/C / ethyl acetate / 30 h / 760 Torr
3: pyridine; 4-dimethylaminopyridine / CH2Cl2 / 10 h / Heating
4: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C
5: Ag2O; CaSO4 / 20 h
6: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
7: MgSO4 / acetonitrile / 1 h
8: aq. HCl / tetrahydrofuran / 30 h / 20 °C
9: pyridine / 96 h / 20 °C
View Scheme
(1S,2R,3S,4S,7S)-3-(Fluoro-dimethyl-silanyl)-5-oxo-7-(toluene-4-sulfonyloxymethyl)-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester
871938-45-3

(1S,2R,3S,4S,7S)-3-(Fluoro-dimethyl-silanyl)-5-oxo-7-(toluene-4-sulfonyloxymethyl)-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C
2: Ag2O; CaSO4 / 20 h
3: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
4: MgSO4 / acetonitrile / 1 h
5: aq. HCl / tetrahydrofuran / 30 h / 20 °C
6: pyridine / 96 h / 20 °C
View Scheme
(3R,4aS,5S,6R,7R,8aS)-3-Cyano-7-hydroxy-6-methoxy-2-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-decahydro-isoquinoline-5-carboxylic acid methyl ester

(3R,4aS,5S,6R,7R,8aS)-3-Cyano-7-hydroxy-6-methoxy-2-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-decahydro-isoquinoline-5-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. HCl / tetrahydrofuran / 30 h / 20 °C
2: pyridine / 96 h / 20 °C
View Scheme
(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-7-methoxy-hexahydro-benzofuran-4,7a-dicarboxylic acid dimethyl ester
185810-96-2

(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-7-methoxy-hexahydro-benzofuran-4,7a-dicarboxylic acid dimethyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: pivalic acid / benzene / Heating
2: pivalic acid / toluene / Heating
3: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
4: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
5: aq. HF / acetonitrile / 0.5 h / Ambient temperature
6: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
7: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
8: aq. HF / acetonitrile / 3 h / Ambient temperature
9: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
Multi-step reaction with 8 steps
1: 56 mg / pivalic acid / toluene / 0.83 h / Heating
2: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
3: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
4: aq. HF / acetonitrile / 0.5 h / Ambient temperature
5: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
6: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
7: aq. HF / acetonitrile / 3 h / Ambient temperature
8: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-2-oxo-hexahydro-benzofuran-4,7a-dicarboxylic acid dimethyl ester
185810-94-0

(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-2-oxo-hexahydro-benzofuran-4,7a-dicarboxylic acid dimethyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature
2: pivalic acid / benzene / Heating
3: pivalic acid / toluene / Heating
4: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
5: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
6: aq. HF / acetonitrile / 0.5 h / Ambient temperature
7: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
8: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
9: aq. HF / acetonitrile / 3 h / Ambient temperature
10: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
Multi-step reaction with 9 steps
1: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature
2: 56 mg / pivalic acid / toluene / 0.83 h / Heating
3: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
4: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
5: aq. HF / acetonitrile / 0.5 h / Ambient temperature
6: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
7: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
8: aq. HF / acetonitrile / 3 h / Ambient temperature
9: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-2-oxo-hexahydro-benzofuran-4,7a-dicarboxylic acid 4-methyl ester
1055030-50-6

(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-2-oxo-hexahydro-benzofuran-4,7a-dicarboxylic acid 4-methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: diethyl ether / 0.08 h / 0 °C
2: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature
3: pivalic acid / benzene / Heating
4: pivalic acid / toluene / Heating
5: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
6: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
7: aq. HF / acetonitrile / 0.5 h / Ambient temperature
8: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
9: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
10: aq. HF / acetonitrile / 3 h / Ambient temperature
11: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
Multi-step reaction with 10 steps
1: diethyl ether / 0.08 h / 0 °C
2: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature
3: 56 mg / pivalic acid / toluene / 0.83 h / Heating
4: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
5: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
6: aq. HF / acetonitrile / 0.5 h / Ambient temperature
7: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
8: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
9: aq. HF / acetonitrile / 3 h / Ambient temperature
10: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2R,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
185811-08-9

(1S,2R,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. HF / acetonitrile / 3 h / Ambient temperature
2: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
1053614-44-0

(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
2: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
3: aq. HF / acetonitrile / 3 h / Ambient temperature
4: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2S,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-6-methoxy-2-{2-[(Z)-2-(6-methoxy-1H-indol-3-yl)-ethylimino]-ethyl}-cyclohexane-1,3-dicarboxylic acid dimethyl ester

(1S,2S,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-6-methoxy-2-{2-[(Z)-2-(6-methoxy-1H-indol-3-yl)-ethylimino]-ethyl}-cyclohexane-1,3-dicarboxylic acid dimethyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: pivalic acid / toluene / Heating
2: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
3: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
4: aq. HF / acetonitrile / 0.5 h / Ambient temperature
5: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
6: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
7: aq. HF / acetonitrile / 3 h / Ambient temperature
8: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1-trimethylsilanyloxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
185811-05-6

(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1-trimethylsilanyloxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: aq. HF / acetonitrile / 0.5 h / Ambient temperature
2: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
3: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
4: aq. HF / acetonitrile / 3 h / Ambient temperature
5: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2S,3R,4aS,13bR,14aS)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
1054654-18-0

(1S,2S,3R,4aS,13bR,14aS)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
2: aq. HF / acetonitrile / 3 h / Ambient temperature
3: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-5-oxo-1-trimethylsilanyloxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
185811-02-3

(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-5-oxo-1-trimethylsilanyloxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
2: aq. HF / acetonitrile / 0.5 h / Ambient temperature
3: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
4: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
5: aq. HF / acetonitrile / 3 h / Ambient temperature
6: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,11-dimethoxy-5-oxo-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
185810-98-4

(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,11-dimethoxy-5-oxo-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

reserpine
50-55-5

reserpine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
2: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
3: aq. HF / acetonitrile / 0.5 h / Ambient temperature
4: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
5: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
6: aq. HF / acetonitrile / 3 h / Ambient temperature
7: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme
reserpine
50-55-5

reserpine

methyl reserpate
2901-66-8

methyl reserpate

Conditions
ConditionsYield
With methanol; sodium methylate for 4h; Reflux;97%
With potassium hydroxide Hydrolysis;
With sodium methylate Hydrolysis;
Stage #1: reserpine With methanol; sodium methylate for 1h; Heating / reflux;
Stage #2: With hydrogenchloride; methanol; water pH=1;
Stage #3: With ammonia; water Product distribution / selectivity;
With sodium methylate In methanol for 1h; Heating / reflux;
reserpine
50-55-5

reserpine

methyl iodide
74-88-4

methyl iodide

N-methylreserpine
60634-65-3

N-methylreserpine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 2h;83%
reserpine
50-55-5

reserpine

(1S,4R,5aS,14bR,15aS,16R)-12,16-dimethoxy-4,5,5a,6,8,9,14,14b,15,15a-decahydro-1,4-methanoindolo[2,3-a]-oxepino[4,5-g]quinolizin-2(1H)-one
6811-42-3

(1S,4R,5aS,14bR,15aS,16R)-12,16-dimethoxy-4,5,5a,6,8,9,14,14b,15,15a-decahydro-1,4-methanoindolo[2,3-a]-oxepino[4,5-g]quinolizin-2(1H)-one

Conditions
ConditionsYield
With aluminum isopropoxide In xylene for 6h; Heating;81%
With aluminum isopropoxide In xylene for 6h; Product distribution / selectivity; Heating / reflux;81%
With aluminum isopropoxide; xylene
reserpine
50-55-5

reserpine

reserpic acid lactone

reserpic acid lactone

Conditions
ConditionsYield
With aluminum isopropoxide In xylene for 6h; Product distribution / selectivity; Heating / reflux;81%
reserpine
50-55-5

reserpine

3-hydroxy-2-methyl-1-propene
513-42-8

3-hydroxy-2-methyl-1-propene

(1S,2R,3R,4aS,13bR,14aS)-methyl-2,11-dimethoxy-13-(2-methylallyl)-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]-pyrido[1,2-b]isoquinoline-1-carboxylate

(1S,2R,3R,4aS,13bR,14aS)-methyl-2,11-dimethoxy-13-(2-methylallyl)-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]-pyrido[1,2-b]isoquinoline-1-carboxylate

Conditions
ConditionsYield
With titanium(IV) isopropylate; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; Inert atmosphere; Schlenk technique;66%
reserpine
50-55-5

reserpine

propargyl bromide
106-96-7

propargyl bromide

A

C36H42N2O9
1227009-31-5

C36H42N2O9

B

reserpine
1227009-32-6

reserpine

Conditions
ConditionsYield
Stage #1: reserpine With sodium hydride In N,N-dimethyl-formamide; mineral oil at -20℃; for 0.25h;
Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene; mineral oil at -20℃; for 1h;
A 30%
B 63%
reserpine
50-55-5

reserpine

dioxyreserpine
127518-55-2

dioxyreserpine

Conditions
ConditionsYield
With oxygen; 1,5-Dichloroanthraquinone In acetonitrile at 20℃; for 2.5h; Sealed tube; Inert atmosphere; Irradiation;63%
reserpine
50-55-5

reserpine

11,17-dimethoxy-4-oxy-18-(3,4,5-trimethoxy-benzoyloxy)-yohimbane-16-carboxylic acid methyl ester
474-48-6

11,17-dimethoxy-4-oxy-18-(3,4,5-trimethoxy-benzoyloxy)-yohimbane-16-carboxylic acid methyl ester

Conditions
ConditionsYield
With dihydrogen peroxide In acetone at 50℃; for 24h;60%
With monoperoxyphthalic acid
With Perbenzoic acid
reserpine
50-55-5

reserpine

allyl methyl carbonate
35466-83-2

allyl methyl carbonate

C36H44N2O9

C36H44N2O9

Conditions
ConditionsYield
Stage #1: allyl methyl carbonate With tris(dibenzylideneacetone)dipalladium (0); trifuran-2-yl-phosphane In dichloromethane at 20℃; Inert atmosphere;
Stage #2: reserpine In dichloromethane at 20℃; Inert atmosphere;
60%
reserpine
50-55-5

reserpine

butanoic acid anhydride
106-31-0

butanoic acid anhydride

A

10-butyryl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

10-butyryl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

B

12-butyryl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

12-butyryl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 56%
B 17%
reserpine
50-55-5

reserpine

propionyl chloride
79-03-8

propionyl chloride

A

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-12-propionyl-3β,20α-yohimban

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-12-propionyl-3β,20α-yohimban

B

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-10-propionyl-3β,20α-yohimban

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-10-propionyl-3β,20α-yohimban

C

16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-10-propionyl-3β,20α-yohimban

16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-10-propionyl-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 16%
B 56%
C 3%
reserpine
50-55-5

reserpine

(1S,2R,3R,4aS,8aS,13aR,13bR,14aS)-2,11-Dimethoxy-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

(1S,2R,3R,4aS,8aS,13aR,13bR,14aS)-2,11-Dimethoxy-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium cyanoborohydride In trifluoroacetic acid for 1h; Ambient temperature;55%
reserpine
50-55-5

reserpine

Hexanoyl chloride
142-61-0

Hexanoyl chloride

A

16β-carbomethoxy-10-hexanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

16β-carbomethoxy-10-hexanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

B

16β-carbomethoxy-12-hexanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

16β-carbomethoxy-12-hexanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 55%
B 16%
reserpine
50-55-5

reserpine

Heptanoic acid chloride
2528-61-2

Heptanoic acid chloride

A

16β-carbomethoxy-10-heptanoyl-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-3β,20α-yohimban

16β-carbomethoxy-10-heptanoyl-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-3β,20α-yohimban

B

16β-carbomethoxy-10-heptanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

16β-carbomethoxy-10-heptanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

C

16β-carbomethoxy-12-heptanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

16β-carbomethoxy-12-heptanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 2%
B 55%
C 18%
reserpine
50-55-5

reserpine

acetic anhydride
108-24-7

acetic anhydride

A

10-acetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

10-acetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

B

12-acetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

12-acetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

C

10,12-diacetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-3β,20α-yohimban

10,12-diacetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 54%
B 14%
C 2%
reserpine
50-55-5

reserpine

n-valeryl chloride
638-29-9

n-valeryl chloride

A

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-10-valeryl-3β,20α-yohimban

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-10-valeryl-3β,20α-yohimban

B

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-12-valeryl-3β,20α-yohimban

16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-12-valeryl-3β,20α-yohimban

C

16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-10-valeryl-3β,20α-yohimban

16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-10-valeryl-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 51%
B 18%
C 4%
reserpine
50-55-5

reserpine

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

A

12-capryloyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

12-capryloyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

B

10-capryloyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

10-capryloyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

C

10-capryloyl-16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-3β,20α-yohimban

10-capryloyl-16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-3β,20α-yohimban

Conditions
ConditionsYield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;A 18%
B 50%
C 2%
reserpine
50-55-5

reserpine

methyl (1R,15S,17R,18R,19S,20S)-17-[(4-hydroxy-3,5-dimethoxyphenyl)carbonyloxy]-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraene-19-carboxylate
21432-74-6

methyl (1R,15S,17R,18R,19S,20S)-17-[(4-hydroxy-3,5-dimethoxyphenyl)carbonyloxy]-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraene-19-carboxylate

Conditions
ConditionsYield
Stage #1: reserpine With aluminum (III) chloride In dichloromethane for 2h;
Stage #2: With hydrogenchloride In dichloromethane; water for 0.0833333h; Product distribution / selectivity;
47.1%
Stage #1: reserpine With aluminum (III) chloride In acetonitrile at 25℃; for 2h;
Stage #2: With hydrogenchloride In water; acetonitrile for 0.0833333h; Product distribution / selectivity;
22.4%
Stage #1: reserpine With aluminum tri-bromide In dichloromethane at 25℃; for 2h;
Stage #2: With hydrogenchloride In dichloromethane; water for 0.0833333h; Product distribution / selectivity;
22.4%
reserpine
50-55-5

reserpine

A

hydroxyindolenine

hydroxyindolenine

B

7-hydroperoxy-7H-reserpine
127518-54-1

7-hydroperoxy-7H-reserpine

C

dioxyreserpine
127518-55-2

dioxyreserpine

Conditions
ConditionsYield
With oxygen In acetonitrile for 2.5h; Irradiation; Inert atmosphere;A n/a
B n/a
C 46%
reserpine
50-55-5

reserpine

formaldehyd
50-00-0

formaldehyd

(1S,2R,3R,4aS,8aS,13aR,13bR,14aS)-2,11-Dimethoxy-10,13-dimethyl-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

(1S,2R,3R,4aS,8aS,13aR,13bR,14aS)-2,11-Dimethoxy-10,13-dimethyl-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium cyanoborohydride; trifluoroacetic acid In water at -5 - 20℃; for 0.75h; Mechanism; other indole alkaloids like tetraphylline, epireserpine, and reserpine; also AcOH as reagent; var. temp. and time;44.5%
With sodium cyanoborohydride; trifluoroacetic acid In water a) -5 deg C, 15 min, b) RT, 30 min;44.5%
reserpine
50-55-5

reserpine

formaldehyd
50-00-0

formaldehyd

7-2H-1,10-dimethyl-2,7-dihydroreserpine

7-2H-1,10-dimethyl-2,7-dihydroreserpine

Conditions
ConditionsYield
With trifluoroacetic acid-d1; sodium cyanoborohydride In water at 0℃; for 0.5h;42%
reserpine
50-55-5

reserpine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-(tert-butyloxycarbonyl)reserpine
913379-66-5

N-(tert-butyloxycarbonyl)reserpine

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 12h;38%
reserpine
50-55-5

reserpine

A

Isoreserpin
482-85-9

Isoreserpin

B

(6aS,8R,9R,10S,10aS,11aS)-2-(2-Amino-4-methoxy-phenyl)-9-methoxy-8-(3,4,5-trimethoxy-benzoyloxy)-3,6,6a,7,8,9,10,10a,11,11a-decahydro-4H-pyrido[1,2-b]isoquinoline-10-carboxylic acid methyl ester
257622-17-6

(6aS,8R,9R,10S,10aS,11aS)-2-(2-Amino-4-methoxy-phenyl)-9-methoxy-8-(3,4,5-trimethoxy-benzoyloxy)-3,6,6a,7,8,9,10,10a,11,11a-decahydro-4H-pyrido[1,2-b]isoquinoline-10-carboxylic acid methyl ester

C

2,7-dihydroisoreserpine

2,7-dihydroisoreserpine

Conditions
ConditionsYield
With trifluoroacetic acid; zinc for 4h; Reduction; Heating;A 10%
B 15%
C 35%
reserpine
50-55-5

reserpine

para-tert-butylphenol
98-54-4

para-tert-butylphenol

N-(hepta-3,5-diyn-1-yl)-N-(penta-1,3-diyn-1-yl)methanesulfonamide

N-(hepta-3,5-diyn-1-yl)-N-(penta-1,3-diyn-1-yl)methanesulfonamide

C56H67N3O12S

C56H67N3O12S

Conditions
ConditionsYield
In benzene at 85℃; for 16h; Diels-Alder Cycloaddition; Sealed tube; regioselective reaction;35%
reserpine
50-55-5

reserpine

A

7-hydroperoxy-7H-reserpine
127518-54-1

7-hydroperoxy-7H-reserpine

B

dioxyreserpine
127518-55-2

dioxyreserpine

Conditions
ConditionsYield
With oxygen In chloroform for 360h; Mechanism; Ambient temperature; Irradiation; also with deuterated substrate;A 5.8%
B 28.1%
With oxygen In chloroform for 15h; Ambient temperature; Irradiation;A 5.8%
B 28.1%
With oxygen In chloroform for 2.5h; Inert atmosphere; Irradiation;
reserpine
50-55-5

reserpine

hydroxyindolenine

hydroxyindolenine

Conditions
ConditionsYield
Stage #1: reserpine With lead acetate In dichloromethane at 0℃; for 1.33333h; Inert atmosphere; Irradiation;
Stage #2: With sodium methylate In methanol at 0℃; for 2.5h; Inert atmosphere; Irradiation;
9%
reserpine
50-55-5

reserpine

Isoreserpin
482-85-9

Isoreserpin

Conditions
ConditionsYield
With acetic anhydride
With acetic acid; trichloroacetic acid
With trifluoroacetic acid epimerization; Heating;
With hydrogenchloride In methanol at 68℃; for 12h; Mechanism;280 mg
With hydrogenchloride In methanol for 72h; Heating;18 g
reserpine
50-55-5

reserpine

11,17-dimethoxy-18-(3,4,5-trimethoxy-benzoyloxy)-yohimb-2-ene-16-carboxylic acid methyl ester

11,17-dimethoxy-18-(3,4,5-trimethoxy-benzoyloxy)-yohimb-2-ene-16-carboxylic acid methyl ester

Conditions
ConditionsYield
With mercury(II) diacetate
With sodium nitrite
reserpine
50-55-5

reserpine

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimba-3,5-dienium; chloride
119720-94-4

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimba-3,5-dienium; chloride

Conditions
ConditionsYield
With lead(IV) acetate; acetic acid Behandeln des Reaktionsprodukts mit wss.HCl;
reserpine
50-55-5

reserpine

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimba-3,5-dienium; perchlorate

ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimba-3,5-dienium; perchlorate

Conditions
ConditionsYield
With methanol; palladium; maleic acid Behandeln der Reaktionsloesung mit HClO4;
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