{[3,5-Bis(trifluoromethyl)phenyl]methyl}(methyl)amine → (2S,4S)-4-[(3,5-Bis-trifluoromethyl-benzyl)-methyl-amino]-1-(3-chloro-benzyl)-pyrrolidine-2-carboxylic acid methyl ester

HRID 490643Notes

Reaction equation

HRID 490643 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C:8](=O)[CH2:7][N:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)=[O:4].[F:19][C:20]([F:35])([F:34])[C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:24][NH:25][CH3:26]>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([N:25]([CH2:24][C:23]2[CH:27]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:29]=[C:21]([C:20]([F:19])([F:34])[F:35])[CH:22]=2)[CH3:26])[CH2:7][N:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)=[O:4]

Participants

3

Reactant 2

HCID 10956204{[3,5-Bis(trifluoromethyl)phenyl]methyl}(methyl)amineHCID 67546544(S)-1-(3-chloro-benzyl)-4-oxo-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 86625307(2S,4S)-4-[(3,5-Bis-trifluoromethyl-benzyl)-methyl-amino]-1-(3-chloro-benzyl)-pyrrolidine-2-carboxylic acid methyl esterYield 95%

Procedure

As described for Example 64c, (S)-1-(3-chloro-benzyl)-4-oxo-pyrrolidine-2-carboxylic acid methyl ester (7 mmol) was converted, using (3,5-bis-trifluoromethyl-benzyl)-methyl-amine instead of (2,4-difluorobenzyl)-methyl-amine, to the title product in 95% yield as yellow oil. MS m/e=509.9 [M+H]+.

Sources & evidence

ORD record
ord-609c27afbfe24b88b39e6e318b9910d7
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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