(5R,7R,8aR)-5-[(Dimethyl-phenyl-silanyl)-methyl]-7-methyl-4-trifluoromethanesulfonyloxy-3,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester

Base Information

Chemical Name:(5R,7R,8aR)-5-[(Dimethyl-phenyl-silanyl)-methyl]-7-methyl-4-trifluoromethanesulfonyloxy-3,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester
CAS No.:223545-36-6
Molecular Formula:C₂₇H₃₂F₃NO₅SSi
Molecular Weight:567.701
Hs Code.:

(5R,7R,8aR)-5-[(Dimethyl-phenyl-silanyl)-methyl]-7-methyl-4-trifluoromethanesulfonyloxy-3,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester

Synonyms:(5R,7R,8aR)-5-[(Dimethyl-phenyl-silanyl)-methyl]-7-methyl-4-trifluoromethanesulfonyloxy-3,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester

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Chemical Property of (5R,7R,8aR)-5-[(Dimethyl-phenyl-silanyl)-methyl]-7-methyl-4-trifluoromethanesulfonyloxy-3,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester

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Technology Process of (5R,7R,8aR)-5-[(Dimethyl-phenyl-silanyl)-methyl]-7-methyl-4-trifluoromethanesulfonyloxy-3,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester

There total 10 articles about (5R,7R,8aR)-5-[(Dimethyl-phenyl-silanyl)-methyl]-7-methyl-4-trifluoromethanesulfonyloxy-3,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

: 107735-20-6
[(dimethylphenylsilyl)methyl]magnesium chloride

: 145100-51-2
N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

: 223545-34-4
(7R,8aR)-7-Methyl-4-oxo-3,4,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester

: 223545-36-6
(5R,7R,8aR)-5-[(Dimethyl-phenyl-silanyl)-methyl]-7-methyl-4-trifluoromethanesulfonyloxy-3,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester

Guidance literature:: [(dimethylphenylsilyl)methyl]magnesium chloride; (7R,8aR)-7-Methyl-4-oxo-3,4,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester; With copper(l) iodide; In diethyl ether; Inert atmosphere;

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; Inert atmosphere; Heating;
DOI:10.1021/jo1019688

Reference yield:

: 223545-26-4
(R)-2-((R)-2-Methyl-pent-4-enyl)-2,3-dihydro-1H-pyridin-4-one

: 223545-36-6
(5R,7R,8aR)-5-[(Dimethyl-phenyl-silanyl)-methyl]-7-methyl-4-trifluoromethanesulfonyloxy-3,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / n-BuLi

2: 86 percent / L-selectride, BF₃*OEt₂ / tetrahydrofuran / -23 °C

3: 1.) O₃, 2.) Me₂S / 1.) MeOH

4: 84 percent / p-TsOH / benzene / 45 - 50 °C

5: 1.) CuI, 2.) DMPU / 1.) Et₂O, 2.) reflux

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide; n-butyllithium; dimethylsulfide; boron trifluoride diethyl etherate; L-Selectride; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; benzene;
DOI:10.1021/jo990192k

Reference yield:

: 223545-30-0
(2R)-2-[(R)-2-methyl-4-pentenyl]-1-(phenoxycarbonyl)-2,3,5,6-tetrahydro-4-pyridone

: 223545-36-6
(5R,7R,8aR)-5-[(Dimethyl-phenyl-silanyl)-methyl]-7-methyl-4-trifluoromethanesulfonyloxy-3,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) O₃, 2.) Me₂S / 1.) MeOH

2: 84 percent / p-TsOH / benzene / 45 - 50 °C

3: 1.) CuI, 2.) DMPU / 1.) Et₂O, 2.) reflux

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide; dimethylsulfide; toluene-4-sulfonic acid; ozone; In benzene;
DOI:10.1021/jo990192k