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inquiryDayangchem'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
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inquiryOur 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
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inquiryWITH 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
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inquiry1.In No Less 10 years exporting experience. you can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specializ
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inquiryHello, 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
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inquiryHenan 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
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inquiryBest quality & Attractive price & Professional service; Trial & Pilot & Commercial Hisunny Chemical is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality intermediates, specia
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inquiryCompany Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments
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inquiry180468-42-2--Ethyl (S)-1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate Appearance:White Powder Storage:Room temperature Package:according to customers' requirements Application:Pharmaceutical intermediates Transportation:By air(EMS or EUB or
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inquiryJ&H CHEM 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. J&H CHEM has some Manufacturing base in Jia
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inquiryfactory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin
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inquiryMassive Chemical is certified with ISO9001 and ISO14001 manufacturer for this product. We will offer all documents as requirement for the materials which includes, Certificate of Analysis, Material Safety Data Sheet, and Method of Analysis and
Cas:180468-42-2
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inquirySuperior quality, moderate price & quick delivery. Appearance:white crystal powder Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:10g/bag,or as your request Application:Used as Pharmaceutical Intermediates Tr
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inquiryOur company was built in 2009 with an ISO certificate.In the past 6 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
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inquiryProduct name: (S)-Ethyl 1-Phenyl-3,4-Dihydroisoquinoline-2(1H)-Carboxylate CAS No.:180468-42-2 Molecule Formula:C18H19NO2 Molecule Weight:281.35 Purity: 98.0% Package: 25kg/drum Description:White or almost white crystalline powder Man
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inquiryWe Huarong Pharm can provide Customized Synthesis & Process R&D & APIs and intermediates Production & Quality Research & Registration Application, especially our GMP validation service which complies with SFDA, FDA, WHO and EU EMPA. O
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inquiryWe are a Union of chemistry in China, consists of chemists,engineers, laboratories,factories in China. We organize surplus capacity of R&D and production as well as custom synthesis for chemical products and chemical business project. We are supp
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inquiryR & D enterprises have their own stock in stockAppearance:To be subject to the object Package:Customized Application:pharmaceutical intermediates Transportation:Air Port:Shanghai;Guangzhou
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inquiryhigh purity,in stock Package:25kg/drum,or as per customers'demand Application:API,or Intermediates,fine chemicals Transportation:air,sea,courier
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inquiryJinhua huayi chemical co., ltd. is dedicated to the development, production and marketing of chemicals. On the basis of equality and mutual benefit, and under the principle of customer first, credit first, quality first, we are ready to join hands
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Min.Order:100 Gram
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inquiryOur clients, like BASF,CHEMO,Brenntag,ASR,Evonik,Merck and etc.Appearance:COA Storage:in stock Application:MSDS/TDS
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inquiryKONING PHARMCHEM CO., LTD. has committed itself to a strategy of providing a unique service for companies involved in the manufacture of pharmaceuticals, healthcare products, food, cosmetics and other fine chemicals. Our products including but not li
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inquirychloroformic acid ethyl ester
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 20℃; | 100% |
With triethylamine In dichloromethane at 20℃; for 5h; | 99% |
With potassium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 2h; Reagent/catalyst; Concentration; | 97.9% |
ethyl bromide
carbon dioxide
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With sodium carbonate In 1,4-dioxane at 25℃; under 750.075 Torr; for 5h; | 84% |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 12h; enantioselective reaction; | 71% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Cooling with ice; | 71% |
1-phenyl-3,4-dihydroisoquinoline
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaBH4 / ethanol / 60 h / 20 °C 2: 100 percent / K2CO3 / CH2Cl2 / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: methanol; sodium tetrahydroborate / water / 5.42 h / 20 - 34 °C 2.1: D-tartaric acid / methanol; ethyl acetate / 2.08 h / 28 - 64 °C / Resolution of racemate 2.2: 1.17 h / pH 8 - 9 3.1: sodium carbonate / toluene / 2.17 h / 0 - 28 °C View Scheme |
N-phenethylbenzamide
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: P2O5; POCl3 / xylene / 2.5 h / Heating 2: NaBH4 / ethanol / 60 h / 20 °C 3: 100 percent / K2CO3 / CH2Cl2 / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: PPA / water / 4.25 h / 14.9 - 165 °C 1.2: 0.17 h / 28 - 42 °C / pH 2.1 - 7.12 2.1: methanol; sodium tetrahydroborate / water / 5.42 h / 20 - 34 °C 3.1: D-tartaric acid / methanol; ethyl acetate / 2.08 h / 28 - 64 °C / Resolution of racemate 3.2: 1.17 h / pH 8 - 9 4.1: sodium carbonate / toluene / 2.17 h / 0 - 28 °C View Scheme |
(S)-1,2,3,4-tetrahydro-1-phenyl-isoquinoline-2-carboxylic acid
chloroformic acid ethyl ester
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With sodium carbonate In water; toluene at 14.9 - 34.8℃; for 3h; |
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / -10 - 20 °C 2.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C 2.2: 20 °C / pH 9 - 10 3.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate 4.1: acetone / 5 °C / Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium carbonate / dichloromethane / 0 - 25 °C 2.1: sodium hydroxide / ethanol / 75 - 80 °C 2.2: Cooling 3.1: acetone / 5 °C / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / -10 - 20 °C 2.1: hydrogenchloride; water; phosphoric acid / 32 h / 95 - 100 °C 2.2: 20 °C / pH 9 - 10 3.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate 4.1: acetone / 5 °C / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / -10 - 20 °C 2.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C 2.2: 20 °C / pH 9 - 10 3.1: D-tartaric acid / water / Resolution of racemate 3.2: 20 °C 4.1: acetone / 5 °C / Reflux View Scheme |
4-nitrophenyl-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol / 75 - 80 °C 1.2: Cooling 2.1: triethylamine / dichloromethane / -10 - 20 °C 3.1: hydrogenchloride; water; phosphoric acid / 32 h / 95 - 100 °C 3.2: 20 °C / pH 9 - 10 4.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate 5.1: acetone / 5 °C / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydroxide / ethanol / 75 - 80 °C 1.2: Cooling 2.1: acetone / 5 °C / Reflux View Scheme |
1-phenyl-1,2,3,4-tetrahydroisoquinoline
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate 2: acetone / 5 °C / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: D-tartaric acid / water / Resolution of racemate 1.2: 20 °C 2.1: acetone / 5 °C / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: D-tartaric acid / water / Resolution of racemate 1.2: 20 °C 2.1: potassium carbonate / dichloromethane / 0 - 25 °C 3.1: sodium hydroxide / ethanol / 75 - 80 °C 3.2: Cooling 4.1: acetone / 5 °C / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: D-tartaric acid / methanol; ethyl acetate / 2.08 h / 28 - 64 °C / Resolution of racemate 1.2: 1.17 h / pH 8 - 9 2.1: sodium carbonate / toluene / 2.17 h / 0 - 28 °C View Scheme |
N-acetyl-(1R)-phenyl-1,2,3,4-tetrahydroisoquinoline
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; water; phosphoric acid / 32 h / 95 - 100 °C 1.2: 20 °C / pH 9 - 10 2.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate 3.1: acetone / 5 °C / Reflux View Scheme |
N-chloroacetyl-(1R)-phenyl-1,2,3,4-tetrahydroisoquinoline
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C 1.2: 20 °C / pH 9 - 10 2.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate 3.1: acetone / 5 °C / Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C 1.2: 20 °C / pH 9 - 10 2.1: D-tartaric acid / water / Resolution of racemate 2.2: 20 °C 3.1: acetone / 5 °C / Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C 1.2: 20 °C / pH 9 - 10 2.1: D-tartaric acid / water / Resolution of racemate 2.2: 20 °C 3.1: potassium carbonate / dichloromethane / 0 - 25 °C 4.1: sodium hydroxide / ethanol / 75 - 80 °C 4.2: Cooling 5.1: acetone / 5 °C / Reflux View Scheme |
1-phenyl-3,4-dihydroisoquinoline
diethyl dicarbonate
A
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
B
ethyl (R)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-3,5-diMe-Synphos; hydrogen In 1,4-dioxane at 40℃; under 22502.3 Torr; for 18h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; |
N-benzyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogen; hydrogenchloride; 5%-palladium/activated carbon / ethanol; ethyl acetate / 24 h / 20 °C / 760.05 Torr / Schlenk technique 2: triethylamine / dichloromethane / 5 h / 20 °C View Scheme |
C22H18N(1+)*Br(1-)
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; (+)-(R)-[2,3,2',3'-tetrahydro-5,5'-bi(1,4-benzodioxin)-6,6'-diyl]bis(diphenylphosphane) / dichloromethane; tetrahydrofuran / 20 h / 30 °C / 31029.7 Torr / Autoclave; Glovebox 2: hydrogen; hydrogenchloride; 5%-palladium/activated carbon / ethanol; ethyl acetate / 24 h / 20 °C / 760.05 Torr / Schlenk technique 3: triethylamine / dichloromethane / 5 h / 20 °C View Scheme |
1-phenylisoquinoline
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: acetone / 24 h / 90 °C 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; (+)-(R)-[2,3,2',3'-tetrahydro-5,5'-bi(1,4-benzodioxin)-6,6'-diyl]bis(diphenylphosphane) / dichloromethane; tetrahydrofuran / 20 h / 30 °C / 31029.7 Torr / Autoclave; Glovebox 3: hydrogen; hydrogenchloride; 5%-palladium/activated carbon / ethanol; ethyl acetate / 24 h / 20 °C / 760.05 Torr / Schlenk technique 4: triethylamine / dichloromethane / 5 h / 20 °C View Scheme |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / methanol; 1,4-dioxane / 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C 2.2: 1 h / 20 °C View Scheme |
2-(2-bromoethyl)benzaldehyde
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: copper(II) sulfate / dichloromethane / 20 h / 23 °C 2.1: toluene; diethyl ether / 3 h / -40 - 25 °C / Inert atmosphere 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C 4.1: hydrogenchloride / methanol; 1,4-dioxane / 1 h / 0 - 20 °C 5.1: triethylamine / dichloromethane / 0.17 h / 0 °C 5.2: 1 h / 20 °C View Scheme |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: toluene; diethyl ether / 3 h / -40 - 25 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C 3.1: hydrogenchloride / methanol; 1,4-dioxane / 1 h / 0 - 20 °C 4.1: triethylamine / dichloromethane / 0.17 h / 0 °C 4.2: 1 h / 20 °C View Scheme |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C 2.1: hydrogenchloride / methanol; 1,4-dioxane / 1 h / 0 - 20 °C 3.1: triethylamine / dichloromethane / 0.17 h / 0 °C 3.2: 1 h / 20 °C View Scheme |
triphenylboroxine
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: (R)-N-(4,4-dimethyl-2-methylenepentyl)-2-methylpropane-2-sulfinamide; chlorobis(cyclooctene)rhodium(I) dimer / toluene / 0.5 h / 20 °C / Inert atmosphere 1.2: 6 h / 60 °C / Inert atmosphere 2.1: Trimethylenediamine / 0.5 h / 20 °C / Microwave irradiation 3.1: triethylamine / dichloromethane / 6 h / 20 °C 3.2: 6 h / 20 °C 4.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12 h / 20 °C View Scheme |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: Trimethylenediamine / 0.5 h / 20 °C / Microwave irradiation 2.1: triethylamine / dichloromethane / 6 h / 20 °C 2.2: 6 h / 20 °C 3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: Trimethylenediamine / 2.5 h / 120 °C / Microwave irradiation 2: triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Cooling with ice 4: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere; Cooling with ice View Scheme |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: (R)-N-(4,4-dimethyl-2-methylenepentyl)-2-methylpropane-2-sulfinamide; chlorobis(cyclooctene)rhodium(I) dimer / toluene / 0.5 h / 20 °C / Inert atmosphere 1.2: 6 h / 60 °C / Inert atmosphere 2.1: Trimethylenediamine / 0.5 h / 20 °C / Microwave irradiation 3.1: triethylamine / dichloromethane / 6 h / 20 °C 3.2: 6 h / 20 °C 4.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: C18H31NOS; [RhCl(cis-cyclooctene)2]2 / toluene / 0.5 h / 20 °C / Inert atmosphere; Schlenk technique 1.2: 6 h / 60 °C 2.1: Trimethylenediamine / 2.5 h / 120 °C / Microwave irradiation 3.1: triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Cooling with ice 5.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere; Cooling with ice View Scheme |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 6 h / 20 °C 1.2: 6 h / 20 °C 2.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Cooling with ice 3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere; Cooling with ice View Scheme |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Cooling with ice 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere; Cooling with ice View Scheme |
2-<2-(t-Butyldimethylsilyloxy)ethyl>benzaldehyde
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: titanium(IV) tetraethanolate / tetrahydrofuran / 12 h / Reflux 2.1: C18H31NOS; [RhCl(cis-cyclooctene)2]2 / toluene / 0.5 h / 20 °C / Inert atmosphere; Schlenk technique 2.2: 6 h / 60 °C 3.1: Trimethylenediamine / 2.5 h / 120 °C / Microwave irradiation 4.1: triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C / Cooling with ice 6.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere; Cooling with ice View Scheme |
benzoyl chloride
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium carbonate / water / 0.25 h / 29.8 °C 1.2: 4.33 h / 17.5 - 26.6 °C 2.1: PPA / water / 4.25 h / 14.9 - 165 °C 2.2: 0.17 h / 28 - 42 °C / pH 2.1 - 7.12 3.1: methanol; sodium tetrahydroborate / water / 5.42 h / 20 - 34 °C 4.1: D-tartaric acid / methanol; ethyl acetate / 2.08 h / 28 - 64 °C / Resolution of racemate 4.2: 1.17 h / pH 8 - 9 5.1: sodium carbonate / toluene / 2.17 h / 0 - 28 °C View Scheme |
phenethylamine
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium carbonate / water / 0.25 h / 29.8 °C 1.2: 4.33 h / 17.5 - 26.6 °C 2.1: PPA / water / 4.25 h / 14.9 - 165 °C 2.2: 0.17 h / 28 - 42 °C / pH 2.1 - 7.12 3.1: methanol; sodium tetrahydroborate / water / 5.42 h / 20 - 34 °C 4.1: D-tartaric acid / methanol; ethyl acetate / 2.08 h / 28 - 64 °C / Resolution of racemate 4.2: 1.17 h / pH 8 - 9 5.1: sodium carbonate / toluene / 2.17 h / 0 - 28 °C View Scheme |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(R)-quinuclidin-3-ol
solifenacin
Conditions | Yield |
---|---|
With sodium hydride; 1-butyl-3-methylimidazolium Tetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 6h; Temperature; Concentration; | 95.1% |
With sodium hydride In toluene for 3h; Heating; | 89% |
Stage #1: (R)-quinuclidin-3-ol With sodium hydride In toluene; mineral oil at 0℃; for 0.25h; Inert atmosphere; Stage #2: (S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline In toluene; mineral oil at 130℃; for 8h; Inert atmosphere; Dean-Stark; | 88% |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
diphenylamine
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 84% |
With sodium hydride In toluene at 103 - 135℃; Temperature; | 82% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
4-chloro-aniline
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 81% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
4-fluoroaniline
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 78.3% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
2,6-Dichloroaniline
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 77.5% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
3-bromoaniline
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 77.5% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
4-methoxy-aniline
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 77% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
2-bromoaniline
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 74.5% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
benzylamine
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 73% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
phenyl sulfamate
Conditions | Yield |
---|---|
Stage #1: (S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline; phenyl sulfamate With aluminum oxide; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} at 20℃; for 0.0833333h; Stage #2: With bis(tertbutylcarbonyloxy)iodobenzene at 20℃; for 6h; enantioselective reaction; | 73% |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
1-amino-3-methylbenzene
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 70% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
2-Chloroaniline
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 69.6% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
2-methoxy-phenylamine
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 68% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
3-chloro-aniline
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 66% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
meta-fluoroaniline
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 65.7% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
aniline
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 65% |
With sodium hydride In toluene at 110 - 120℃; | 64.7% |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
m-Anisidine
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 63.5% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
2-Fluoroaniline
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 63% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
4-bromo-aniline
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 61.6% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
o-toluidine
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 59.5% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
p-toluidine
Conditions | Yield |
---|---|
With sodium hydride In toluene at 110 - 120℃; | 53% |
With sodium hydride In toluene at 110 - 120℃; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
solifenacin
Conditions | Yield |
---|---|
Stage #1: (3R)-1-azabicyclo[2.2.2]octan-3-ol hydrochloride With sodium methylate at 5 - 30℃; Inert atmosphere; Stage #2: (S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline In N,N-dimethyl-formamide; toluene at 60℃; Reflux; | 51% |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
solifenacin
Conditions | Yield |
---|---|
Stage #1: sodium (R)-quinuclidin-3-ol With sodium methylate In N,N-dimethyl-formamide; toluene at 25℃; Inert atmosphere; Reflux; Stage #2: (S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline In N,N-dimethyl-formamide; toluene at 70℃; Reflux; | 50% |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(R)-quinuclidin-3-ol
A
(1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester
B
(3R)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate
C
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
D
solifenacin
Conditions | Yield |
---|---|
With potassium 2-methylbutan-2-olate In toluene at 90℃; for 3h; Product distribution / selectivity; | A 1.1% B 3.2% C 6% D n/a |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(S)-quinuclidin-3-ol
(1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester
Conditions | Yield |
---|---|
With sodium hydride In toluene Heating; |
(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline
A
(1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester
B
(3R)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate
C
solifenacin
Conditions | Yield |
---|---|
Stage #1: (R)-quinuclidin-3-ol With sodium hydride In toluene for 0.166667h; Stage #2: (S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline In toluene at 26 - 110℃; for 4.33333h; Product distribution / selectivity; |
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