4-Oxo-4-(pyrrolidin-1-yl)butanoic acid → (3aR,4S,7aR)-4-(4-oxo-4-pyrrolidin-1-yl-butyryloxy)-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester

HRID 2176760Notes

Reaction equation

HRID 2176760 reaction equation
[CH3:1][O:2][C:3]([N:5]1[C@@H:13]2[C@@H:8]([C@@:9]([OH:23])([C:14]#[C:15][C:16]3[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=3)[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].[O:24]=[C:25]([N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)[CH2:26][CH2:27][C:28](O)=[O:29]>>[CH3:1][O:2][C:3]([N:5]1[C@H:13]2[C@H:8]([C@:9]([O:23][C:28](=[O:29])[CH2:27][CH2:26][C:25](=[O:24])[N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)([C:14]#[C:15][C:16]3[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=3)[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1)=[O:4]

Participants

3

Reactant 2

HCID 8538084-Oxo-4-(pyrrolidin-1-yl)butanoic acidHCID 68276168(3aS,4R,7aS)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester

Product 1

HCID 60142444(3aR,4S,7aR)-4-(4-oxo-4-pyrrolidin-1-yl-butyryloxy)-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester

Procedure

Synthesis in analogy to the General Method 1 starting from (3aS,4R,7aS)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester and 4-oxo-4-(pyrrolidin-1-yl)-butanoic acid to yield (3aR,4S,7aR)-4-(4-oxo-4-pyrrolidin-1-yl-butyryloxy)-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester. MS [M+H]=467; RT=2.88 min; UPLC Method II

Sources & evidence

ORD record
ord-8aae1af1f63042be8f5a3c31903a7b78
Source dataset
uspto-grants-2015_06
Patent number
US09067881B2

Reaction notes

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