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Hunan Wistar Imp. & Exp. Co., Ltd.

The company serves as a key global supplier of statins intermediates, which has a solid industrial foundation in the field of statins for lipid-lowering drugs, and holds a leading position in the market. Leveraging extensive experience in research an

Buy Quality Top Purity 99% 147489-06-3 Low Price

Cas:147489-06-3

Min.Order:25 Kilogram

Negotiable

Type:Trading Company

inquiry

Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

Jinlan Pharm-Drugs Technology Co.,Limited (with its export company Hangzhou Royall Import & Export Co.,Ltd.)is located in Hangzhou, Zhejiang Province. Neighboring Ningbo port, Shanghai port, Hangzhou Xiaoshan Int’l Airport and Shanghai Pudo

Wuhan Fortuna Chemical Co.,Ltd

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Cas 147489-06-3 Company profile Wuhan Fortuna Chemical Co.,Ltd established in 2006, is a big integrative chemical e

Sinoway Industrial Co., Ltd.

Assay: 99% up; Stable supply with over 50Mt annually; Appearance:white to off-white powder Storage:room temprature Package:25kg/drum Application:Intermediate of Pitavastatin Calcium Port:Beijing/Shanghai/Shenzhen/Hangzhou

Dayang Chem (Hangzhou) Co.,Ltd.

As a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem’s R&D center offer custom synthesis services. DayangChem can provide different quantities of custom synthesis

Hebei yanxi chemical co.,LTD.

Hebei yanxi chemical co., LTD is a professional research, development and production of lead acetate benzene acetamide enterprise backbone members by local well-known entrepreneurs and professional senior engineers in the party's "low carb

t-Butyl (3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-isopropylidenedioxy-6-heptenoate

Cas:147489-06-3

Min.Order:1 Kilogram

FOB Price: $1.0 / 3.0

Type:Trading Company

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

Henan Tianfu Chemical Co., Ltd.

CAS No.147489-06-3 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 S

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

Pharmaceutical Grade CAS 147489-06-3 with competitive price

Cas:147489-06-3

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

Hebei Nengqian Chemical Import and Export Co., LTD

Our Advantage Rich Experience Our products are sold all over Europe,North&South America, Sino-East, Asia and pacific area as well as Africa,we establish long term. Quality service Company cooperates with research institutes. We strictly con

Hubei Langyou International Trading Co., Ltd

1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:White Crystalline Powder Storage:Store in sealed conta

high quality 147489-06-3 Pitavastatin Impurity 15 with best price

Cas:147489-06-3

Min.Order:10 Gram

Negotiable

Type:Other

inquiry

Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients 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 Specialized

Qingdao Beluga Import and Export Co., LTD

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester CAS:147489-06-3 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating resea

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

Hubei Jiutian Bio-medical Technology Co., Ltd

1,we produce and sell good chemicals around the world. 2,our success rate is about 95%. this means, if customer order is accepted, the probability that the customer will obtain the ordered substances, is 95%. 3,our staff consists of highly qualifie

Wuhan Zenuo Biological Medicine Technology Co Ltd

Product Name: (4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester Synonyms: (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-2,2-Dimethyl-1,3-dioxane-6- hept

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

Xiamen Hisunny Chemical Co.,Ltd

Best 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

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

Nanjing Fred Technology Co.,Ltd.

(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester is one of the most competitive products in our company, we can supply it with good quality and best price. Appearance:Wh

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

SHANGHAI T&W PHARMACEUTICAL CO., LTD.

A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc

Saiwante (shanghai) New Material Technology Co., Ltd.

ProName:(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-... CasNo:147489-06-3 Molecular Formula:C32H36FNO4 Appearance:powder Application:cinnamyl (Z)-3-aminobut-2-enoate DeliveryTime:very soon PackAge:25kg/drum Port:Shanghai ProductionCapacity:100 Ki

Hangzhou J&H Chemical Co., Ltd.

J&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

Chemlyte Solutions

Chemlyte Solutions believe that customers and suppliers deserve much more than what traditional distributors can offer. To grow in today s fast-paced and increasingly competitive market it is essential to be able to quickly adapt to market forces eff

Shanghai Massive Chemical Technology Co., Ltd.

Massive 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

Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

Hangzhou Lingrui Chemical Co.,Ltd.

t-Butyl (3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-isopropylidenedioxy-6-heptenoateAppearance:off-white powder Storage:Kept in a cool, dry and ventilated place Package:according to customers' requirements Application:research chemi

SHANGHAI SYSTEAM BIOCHEM CO., LTD

We are one of a few suppliers that can offer custom synthesis service of this product We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to prov

Synthetic route

C21H28N2O6S2

C21H28N2O6S2

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline
121660-37-5

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With sodium t-butanolate In tetrahydrofuran at -10 - 25℃; for 4h;89.6%
C15H24N2O6S2

C15H24N2O6S2

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline
121660-37-5

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 25℃; for 4h;89.3%
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
124752-23-4

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

diethyl <2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methylphosphonate
154057-57-5

diethyl <2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methylphosphonate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With lithium chloride In tetrahydrofuran at 0 - 35℃; for 5.66667h; Reagent/catalyst; Inert atmosphere;89%
With n-butyllithium In tetrahydrofuran at -80 - -10℃; for 1h; Solvent; Temperature; Inert atmosphere;71%
C16H26N2O6S2

C16H26N2O6S2

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline
121660-37-5

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 25℃; for 4h; Temperature;88.3%
2-({[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methyl}sulfonyl)benzo[d]thiazole
1234331-54-4

2-({[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methyl}sulfonyl)benzo[d]thiazole

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
124752-23-4

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -30 - 20℃; Product distribution / selectivity;86%
C18H28N2O6S2

C18H28N2O6S2

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline
121660-37-5

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 25℃; for 4h;82.5%
((2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)methyl)triphenylphosphoniumchloride

((2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)methyl)triphenylphosphoniumchloride

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
124752-23-4

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 30 - 50℃; for 3h; Large scale;80.2%
2-cyclopropyl-4-(4-fluorophenyl)-3-iodoquinoline
153968-97-9

2-cyclopropyl-4-(4-fluorophenyl)-3-iodoquinoline

t-butyl (3R,5S,6E)-3,5-isopropylidenedioxy-7-chlorodimethylsilyl-6-heptenoate
153968-91-3

t-butyl (3R,5S,6E)-3,5-isopropylidenedioxy-7-chlorodimethylsilyl-6-heptenoate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃; for 0.5h;80%
C31H38O4P(1+)*Cl(1-)

C31H38O4P(1+)*Cl(1-)

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline
121660-37-5

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 80 - 85℃; for 1h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;79.2%
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
124752-23-4

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyltriphenylphosphonium bromide

<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyltriphenylphosphonium bromide

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate; <2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyltriphenylphosphonium bromide In dimethyl sulfoxide at 35℃; Large scale;
Stage #2: With potassium carbonate In dimethyl sulfoxide at 70℃; for 4h; Solvent; Time; Temperature; Large scale;
72.3%
With potassium carbonate In dimethyl sulfoxide at 70℃; for 3h; Inert atmosphere;55.8%
With potassium carbonate In dimethyl sulfoxide at 70℃; for 3h; Wittig Reaction;
C19H15BrFNZn

C19H15BrFNZn

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
124752-23-4

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 0 - 30℃; for 16.5h; Reagent/catalyst; Wittig Olefination;66.7%
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
124752-23-4

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyl(diphenyl)phosphine oxide
146578-99-6

<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyl(diphenyl)phosphine oxide

A

tert-butyl (3R,5S,6Z)-7-{2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl}-3,5-isopropylidenedioxy-6-heptenoate

tert-butyl (3R,5S,6Z)-7-{2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl}-3,5-isopropylidenedioxy-6-heptenoate

B

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran for 3h; Ambient temperature; Yield given. Yields of byproduct given;
2-cyclopropyl-4-(4-fluorophenyl)-3-iodoquinoline
153968-97-9

2-cyclopropyl-4-(4-fluorophenyl)-3-iodoquinoline

t-butyl (3R,5S)-3,5-dihydroxy-6-heptynoate
160375-25-7

t-butyl (3R,5S)-3,5-dihydroxy-6-heptynoate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); dimethylmonochlorosilane; tetrabutyl ammonium fluoride; triethyl phosphite; t-Bu3P*Pt(CH2=CH)SiMe2)2O 1.) 1 h, room t., 2.) THF, 60 deg C, 0.5 h; Yield given. Multistep reaction;
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
124752-23-4

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyl(diphenyl)phosphine oxide
146578-99-6

<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyl(diphenyl)phosphine oxide

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With 2,2,6,6-tetramethylpiperidinyl-lithium 1.) THF, RT, 30 min, 2.) THF, 3 h; Yield given. Multistep reaction;
2-cyclopropyl-4-(4-fluorophenyl)-3-{[(1-methyl-1H-benzo[d]imidazol-2-yl)sulfonyl]methyl}quinoline

2-cyclopropyl-4-(4-fluorophenyl)-3-{[(1-methyl-1H-benzo[d]imidazol-2-yl)sulfonyl]methyl}quinoline

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
124752-23-4

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 25 - 35℃; for 3h;
bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 60 percent / Zn / tetrahydrofuran / 1 h / 80 °C
2: 1.) diethylmethoxyborane, 2.) sodium borohydride / 1.) THF, methanol, -78 deg C, 10 min, 2.) THF, methanol, -78 deg C, 3 h
3: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
4: p-toluenesulfonic acid / 2 h / Ambient temperature
5: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature
6: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C
View Scheme
Multi-step reaction with 4 steps
1: 1.) Zn, 2.) HCl aq. / 1.) THF, 1 h, reflux, 2.) 0.5 h
2: 82 percent / NaBH4, Et2BOMe / tetrahydrofuran; methanol / 6 h / -78 °C
3: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
4: 1.) ClMe2SiH, 2.) <(allyl)PdCl>2, TBAF, P(OEt)3 / 1.) t-Bu3P*Pt(CH2=CH)SiMe2)2O / 1.) 1 h, room t., 2.) THF, 60 deg C, 0.5 h
View Scheme
(3S)-5-(t-butyldimethylsilyl)-3-hydroxy-4-pentynenitrile
153968-98-0

(3S)-5-(t-butyldimethylsilyl)-3-hydroxy-4-pentynenitrile

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 60 percent / Zn / tetrahydrofuran / 1 h / 80 °C
2: 1.) diethylmethoxyborane, 2.) sodium borohydride / 1.) THF, methanol, -78 deg C, 10 min, 2.) THF, methanol, -78 deg C, 3 h
3: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
4: p-toluenesulfonic acid / 2 h / Ambient temperature
5: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature
6: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C
View Scheme
Multi-step reaction with 4 steps
1: 1.) Zn, 2.) HCl aq. / 1.) THF, 1 h, reflux, 2.) 0.5 h
2: 82 percent / NaBH4, Et2BOMe / tetrahydrofuran; methanol / 6 h / -78 °C
3: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
4: 1.) ClMe2SiH, 2.) <(allyl)PdCl>2, TBAF, P(OEt)3 / 1.) t-Bu3P*Pt(CH2=CH)SiMe2)2O / 1.) 1 h, room t., 2.) THF, 60 deg C, 0.5 h
View Scheme
t-butyl (3R,5S)-7-(t-butyldimethylsilyl)-3,5-dihydroxy-6-heptynoate
153969-00-7

t-butyl (3R,5S)-7-(t-butyldimethylsilyl)-3,5-dihydroxy-6-heptynoate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
2: p-toluenesulfonic acid / 2 h / Ambient temperature
3: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature
4: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C
View Scheme
Multi-step reaction with 2 steps
1: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
2: 1.) ClMe2SiH, 2.) <(allyl)PdCl>2, TBAF, P(OEt)3 / 1.) t-Bu3P*Pt(CH2=CH)SiMe2)2O / 1.) 1 h, room t., 2.) THF, 60 deg C, 0.5 h
View Scheme
t-butyl (5S)-7-(t-butyldimethylsilyl)-5-hydroxy-3-oxo-6-heptynoate
153968-99-1

t-butyl (5S)-7-(t-butyldimethylsilyl)-5-hydroxy-3-oxo-6-heptynoate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) diethylmethoxyborane, 2.) sodium borohydride / 1.) THF, methanol, -78 deg C, 10 min, 2.) THF, methanol, -78 deg C, 3 h
2: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
3: p-toluenesulfonic acid / 2 h / Ambient temperature
4: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature
5: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1: 82 percent / NaBH4, Et2BOMe / tetrahydrofuran; methanol / 6 h / -78 °C
2: 81 percent / TBAF / tetrahydrofuran / 2 h / 0 °C
3: 1.) ClMe2SiH, 2.) <(allyl)PdCl>2, TBAF, P(OEt)3 / 1.) t-Bu3P*Pt(CH2=CH)SiMe2)2O / 1.) 1 h, room t., 2.) THF, 60 deg C, 0.5 h
View Scheme
t-butyl (3R,5S)-3,5-dihydroxy-6-heptynoate
160375-25-7

t-butyl (3R,5S)-3,5-dihydroxy-6-heptynoate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: p-toluenesulfonic acid / 2 h / Ambient temperature
2: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature
3: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C
View Scheme
t-butyl (3R,5S)-3,5-syn-isopropylidenedioxy-6-heptynoate
153969-01-8

t-butyl (3R,5S)-3,5-syn-isopropylidenedioxy-6-heptynoate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: t-Bu3P*Pt(CH2=CHSiMe2)2O / 1 h / Ambient temperature
2: 80 percent / (η3-allylPdCl)2, TBAF / tetrahydrofuran / 0.5 h / 60 °C
View Scheme
3-(bromomethyl)-2-cyclopropyl-4-(4-fluorophenyl)-quinoline
154057-56-4

3-(bromomethyl)-2-cyclopropyl-4-(4-fluorophenyl)-quinoline

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / toluene / 12 h / Heating
2: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h
View Scheme
Multi-step reaction with 2 steps
1: isopropyl alcohol; toluene / 4 h / 25 - 50 °C / Industry scale
2: potassium carbonate / dimethyl sulfoxide / 10 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1: isopropyl alcohol; toluene / 3 h / 50 °C / Industry scale
2: potassium carbonate / dimethyl sulfoxide / 10 h / 25 °C / Industry scale
View Scheme
Multi-step reaction with 2 steps
1: isopropyl alcohol; toluene / 50 °C
2: potassium carbonate / dimethyl sulfoxide / 10 h / 25 °C / Inert atmosphere; Industry scale
View Scheme
Multi-step reaction with 2 steps
1: toluene / 100 - 110 °C
2: n-butyllithium / tetrahydrofuran / 1 h / -80 - -10 °C / Inert atmosphere
View Scheme
isopropyl (2S,3R,4S,6R)-7-t-butoxycarbonyl-2,3-dihydroxy-4,6-isopropylidenedioxyheptanoate
147489-02-9

isopropyl (2S,3R,4S,6R)-7-t-butoxycarbonyl-2,3-dihydroxy-4,6-isopropylidenedioxyheptanoate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
2: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h
View Scheme
Multi-step reaction with 2 steps
1: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
2: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature
View Scheme
isopropyl (2S,3R,4S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dihydroxyheptanoate
147489-00-7

isopropyl (2S,3R,4S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dihydroxyheptanoate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature
2: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
3: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
4: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h
View Scheme
Multi-step reaction with 4 steps
1: 98 percent / p-TsOH / 2 h / Ambient temperature
2: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
3: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
4: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature
View Scheme
isopropyl (2S,3R,4S,6R)-7-t-butpxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-isopropylidenedioxyheptanoate
147489-01-8

isopropyl (2S,3R,4S,6R)-7-t-butpxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-isopropylidenedioxyheptanoate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
2: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
3: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h
View Scheme
Multi-step reaction with 3 steps
1: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
2: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
3: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature
View Scheme
isopropyl (2S,3S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-6-hydroxy-4-oxoheptanoate
147488-99-1

isopropyl (2S,3S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-6-hydroxy-4-oxoheptanoate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) diethyl(methoxy)borane, 2.) sodium borohydride / 1.) THF, methanol, RT, 15 min, 2.) THF, methanol, a) -78 deg C, 4 h, b) from -78 deg C to RT, 8 h
2: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature
3: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
4: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
5: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h
View Scheme
Multi-step reaction with 5 steps
1: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h
2: 98 percent / p-TsOH / 2 h / Ambient temperature
3: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
4: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
5: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature
View Scheme
isopropyl (2S,3S)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dioxoheptanoate
147488-98-0

isopropyl (2S,3S)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dioxoheptanoate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 60 percent / DIBAL / tetrahydrofuran; hexane / 4 h / -78 °C
2: 1.) diethyl(methoxy)borane, 2.) sodium borohydride / 1.) THF, methanol, RT, 15 min, 2.) THF, methanol, a) -78 deg C, 4 h, b) from -78 deg C to RT, 8 h
3: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature
4: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
5: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
6: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h
View Scheme
Multi-step reaction with 6 steps
1: 60 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -78 °C
2: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h
3: 98 percent / p-TsOH / 2 h / Ambient temperature
4: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
5: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
6: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature
View Scheme
2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline
121660-11-5

2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / phosphorus tribromide / CH2Cl2; toluene / 3 h / Ambient temperature
2: 100 percent / toluene / 12 h / Heating
3: 1.) lithium 2,2,6,6-tetramethylpiperidine / 1.) THF, RT, 30 min, 2.) THF, 3 h
View Scheme
Multi-step reaction with 3 steps
1.1: phosphorus tribromide / dichloromethane / 2 h / 0 - 25 °C / Industry scale
1.2: pH 7 - 8
2.1: isopropyl alcohol; toluene / 4 h / 25 - 50 °C / Industry scale
3.1: potassium carbonate / dimethyl sulfoxide / 10 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1: phosphorus tribromide / dichloromethane / 0 - 25 °C / Industry scale
2: isopropyl alcohol; toluene / 3 h / 50 °C / Industry scale
3: potassium carbonate / dimethyl sulfoxide / 10 h / 25 °C / Industry scale
View Scheme
tert-butyl acetoacetate
1694-31-1

tert-butyl acetoacetate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 74 percent / NaH, n-BuLi / 20 h / -78 °C
2: 60 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -78 °C
3: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h
4: 98 percent / p-TsOH / 2 h / Ambient temperature
5: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
6: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
7: lithium 2,2,6,6-tetramethylpiperazide / tetrahydrofuran / 3 h / Ambient temperature
View Scheme
Cyclopropyl methyl ketone
765-43-5

Cyclopropyl methyl ketone

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: toluene / 0.25 h / 25 °C
1.2: 14 h / 10 - 75 °C / Inert atmosphere
1.3: 0.75 h / 0 - 25 °C / pH 2.5
2.1: sulfuric acid / water; methanol / 22.25 h / 25 - 65 °C
2.2: 0.75 h / 0 - 25 °C / pH 6
3.1: toluene / 5 h / 25 °C / Inert atmosphere
3.2: 3 h
3.3: 2 h / 40 °C
4.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C
View Scheme
Multi-step reaction with 5 steps
1.1: toluene / 0.25 h / 25 °C
1.2: 14 h / 10 - 75 °C / Inert atmosphere
1.3: 0.75 h / 0 - 25 °C / pH 2.5
2.1: sulfuric acid / water; methanol / 22.25 h / 25 - 65 °C
2.2: 0.75 h / 0 - 25 °C / pH 6
3.1: diisobutylaluminium hydride / toluene / 2 h / 0 - 25 °C
3.2: 0.25 h / 10 °C
4.1: phosphorus tribromide / dichloromethane / 1.5 h / 25 °C
4.2: 1 h / 75 °C
5.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C
View Scheme
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

(3R,5S,6E)-7-<2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl>-3,5-dihydroxy-6-heptenoic acid 1,5-lactone

(3R,5S,6E)-7-<2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl>-3,5-dihydroxy-6-heptenoic acid 1,5-lactone

Conditions
ConditionsYield
With hydroxylamine hydrochloride In methanol; water; acetone Reflux;99%
With trifluoroacetic acid74%
With trifluoroacetic acid In dichloromethane for 16h; Ambient temperature;67%
With trifluoroacetic acid In dichloromethane for 16h; Ambient temperature;67%
Stage #1: (4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester With hydrogenchloride; water In acetonitrile at 30℃; for 2h;
Stage #2: With sodium hydroxide In water; acetonitrile at 35℃; for 2h; Product distribution / selectivity;
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoic acid tert-butyl ester
586966-54-3

(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoic acid tert-butyl ester

Conditions
ConditionsYield
With hydrogenchloride In water; acetonitrile at 40℃; for 2h;95.2%
With hydrogenchloride; water In acetonitrile for 3h; Large scale;88.4%
Stage #1: (4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester With water; oxalic acid In methanol at 35℃; for 6h;
Stage #2: With sodium carbonate In methanol; water at 10 - 30℃; for 2.75h; pH=7;
With hydrogenchloride; water In acetonitrile at 25 - 55℃; pH=2.5;27 g
With hydrogenchloride In water; acetonitrile at 13℃; for 2h;
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

pitavastatin
147526-32-7

pitavastatin

Conditions
ConditionsYield
Stage #1: (4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester With trifluoroacetic acid In acetonitrile at 30 - 35℃;
Stage #2: With caesium carbonate In acetonitrile at 35 - 40℃;
94%
Multi-step reaction with 3 steps
1.1: water; oxalic acid / methanol / 6 h / 35 °C
1.2: 2.75 h / 10 - 30 °C / pH 7
2.1: sodium hydroxide; water / methanol / 1.67 h / 0 °C
2.2: 0.67 h / 25 °C
3.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3
View Scheme
Multi-step reaction with 4 steps
1.1: water; oxalic acid / methanol / 6 h / 35 °C
1.2: 2.75 h / 10 - 30 °C / pH 7
2.1: sodium hydroxide; water / acetonitrile / 1.5 h / 30 °C
2.2: 0.25 h / 0 °C / pH 4
2.3: 0.5 h / 0 °C
3.1: sodium hydroxide / water / 0.75 h / 30 °C
3.2: 0.75 h / 35 °C
4.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / acetonitrile; water / 2 h / 13 °C
2: sodium hydroxide / water / 2 h / 10 °C / Large scale
View Scheme

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