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147489-06-3 (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 No: 147489-06-3
USD $ 40.0-50.0 / Gram 1 Gram 1000 Metric Ton/Day WUHAN MULEI NEW MATERIAL CO., LTD Contact Supplier
(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 No: 147489-06-3
USD $ 1560.0-1560.0 / Kilogram 1 Kilogram 100 Kilogram/Month Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd Contact Supplier
t-Butyl (3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-...
Cas No: 147489-06-3
USD $ 500.0-500.0 / Gram 1000 Gram 10 Metric Ton/Month Hebei yanxi chemical co.,LTD. Contact Supplier
2-[6-[2-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert-butyl ester
Cas No: 147489-06-3
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier
[4R-[4α,6α(E)]]-6-{2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-ethenyl}-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester
Cas No: 147489-06-3
No Data No Data No Data Chemwill Asia Co., Ltd. Contact Supplier
(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 No: 147489-06-3
USD $ 2.0-2.0 / Kilogram 1 Kilogram 1-10 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
high quality 147489-06-3 Pitavastatin Impurity 15 with best price
Cas No: 147489-06-3
No Data 10 Gram 1000 Metric Ton/Month Hubei XinRunde Chemical Co., Ltd Contact Supplier
t-Butyl (3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-isopropylidenedioxy-6-heptenoate
Cas No: 147489-06-3
USD $ 1.0-1.0 / Kilogram 1 Kilogram 1000 Kilogram/Day Hubei Jusheng Technology Co., Ltd., Contact Supplier
CAS No.147489-06-3 (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 No: 147489-06-3
No Data 1 Kilogram 5000 Kilogram/Year Henan Tianfu Chemical Co., Ltd. Contact Supplier
New production CAS 147489-06-3 with best quality
Cas No: 147489-06-3
USD $ 139.0-210.0 / Kilogram 1 Kilogram 1000 Kilogram/Day Zhuozhou Wenxi import and Export Co., Ltd Contact Supplier

147489-06-3 Usage

InChI:InChI=1/C32H36FNO4/c1-31(2,3)38-28(35)19-24-18-23(36-32(4,5)37-24)16-17-26-29(20-12-14-22(33)15-13-20)25-8-6-7-9-27(25)34-30(26)21-10-11-21/h6-9,12-17,21,23-24H,10-11,18-19H2,1-5H3/b17-16+/t23-,24-/m1/s1

147489-06-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names (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

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:147489-06-3 SDS

147489-06-3Synthetic 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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