(2S,4aS,5R,8aR)-2-(4-Methoxycarbonyl-2-oxo-butyl)-5-pentyl-octahydro-quinoline-1-carboxylic acid phenyl ester

Base Information

Chemical Name:(2S,4aS,5R,8aR)-2-(4-Methoxycarbonyl-2-oxo-butyl)-5-pentyl-octahydro-quinoline-1-carboxylic acid phenyl ester
CAS No.:109021-42-3
Molecular Formula:C₂₇H₃₉NO₅
Molecular Weight:457.61
Hs Code.:

Synonyms:(2S,4aS,5R,8aR)-2-(4-Methoxycarbonyl-2-oxo-butyl)-5-pentyl-octahydro-quinoline-1-carboxylic acid phenyl ester

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Chemical Property of (2S,4aS,5R,8aR)-2-(4-Methoxycarbonyl-2-oxo-butyl)-5-pentyl-octahydro-quinoline-1-carboxylic acid phenyl ester

Chemical Property:

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Technology Process of (2S,4aS,5R,8aR)-2-(4-Methoxycarbonyl-2-oxo-butyl)-5-pentyl-octahydro-quinoline-1-carboxylic acid phenyl ester

There total 7 articles about (2S,4aS,5R,8aR)-2-(4-Methoxycarbonyl-2-oxo-butyl)-5-pentyl-octahydro-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: 58.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 109021-41-2
(2S,4aS,5R,8aR)-2-((S)-5-Oxo-2,5-dihydro-furan-2-ylmethyl)-5-pentyl-octahydro-quinoline-1-carboxylic acid phenyl ester

: 109021-42-3
(2S,4aS,5R,8aR)-2-(4-Methoxycarbonyl-2-oxo-butyl)-5-pentyl-octahydro-quinoline-1-carboxylic acid phenyl ester

Guidance literature:: With sodium methylate; In methanol; diethyl ether; at 0 ℃; for 0.5h;
DOI:10.1248/cpb.34.2380

Reference yield:

: 92264-05-6
(S)-5-((2R,4aR,5S,8aS)-5-Pentyl-decahydro-quinolin-2-ylmethyl)-dihydro-furan-2-one

: 109021-42-3
(2S,4aS,5R,8aR)-2-(4-Methoxycarbonyl-2-oxo-butyl)-5-pentyl-octahydro-quinoline-1-carboxylic acid phenyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / 4-dimethylaminopyridine / pyridine / 48 h / Ambient temperature

2: 46 percent / lithium isopropylcyclohexylamide, HMPA / tetrahydrofuran / 0.17 h / -73 °C

3: 100 percent / 30 percent H₂O₂, pyridine / CH₂Cl₂ / 0.5 h / 0 °C

4: 58 percent / 5 percent sodium methoxide / methanol; diethyl ether / 0.5 h / 0 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dihydrogen peroxide; sodium methylate; lithium cyclohexylisopropylamide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane;
DOI:10.1248/cpb.34.2380

Reference yield:

: 109021-36-5
(S)-4-Hydroxy-5-((2R,4aR,5S,8aS)-5-pentyl-decahydro-quinolin-2-yl)-pentanoic acid methyl ester

: 109021-42-3
(2S,4aS,5R,8aR)-2-(4-Methoxycarbonyl-2-oxo-butyl)-5-pentyl-octahydro-quinoline-1-carboxylic acid phenyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / p-TsOH / benzene / 1 h / Heating

2: 99 percent / 4-dimethylaminopyridine / pyridine / 48 h / Ambient temperature

3: 46 percent / lithium isopropylcyclohexylamide, HMPA / tetrahydrofuran / 0.17 h / -73 °C

4: 100 percent / 30 percent H₂O₂, pyridine / CH₂Cl₂ / 0.5 h / 0 °C

5: 58 percent / 5 percent sodium methoxide / methanol; diethyl ether / 0.5 h / 0 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dihydrogen peroxide; sodium methylate; lithium cyclohexylisopropylamide; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; benzene;
DOI:10.1248/cpb.34.2380