4-(3-(3,5-Difluorophenyl)propyl)piperidine → 2-(R)-(3-(S)-((4-(3-(3,5-Difluorophenyl)propyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid

HRID 1386754Notes

Reaction equation

HRID 1386754 reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][N:5]([C@H:14]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:15]([O:17]CC2C=CC=CC=2)=[O:16])[CH2:4]1)=O.[F:31][C:32]1[CH:33]=[C:34]([CH2:39][CH2:40][CH2:41][CH:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH:35]=[C:36]([F:38])[CH:37]=1>>[F:31][C:32]1[CH:33]=[C:34]([CH2:39][CH2:40][CH2:41][CH:42]2[CH2:43][CH2:44][N:45]([CH2:1][C@@H:3]3[C@@H:7]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH2:6][N:5]([C@H:14]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[C:15]([OH:17])=[O:16])[CH2:4]3)[CH2:46][CH2:47]2)[CH:35]=[C:36]([F:38])[CH:37]=1

Participants

3

Reactant 2

HCID 211806144-(3-(3,5-Difluorophenyl)propyl)piperidine2×HCID 599246172-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester

Product 1

HCID 206723552-(R)-(3-(S)-((4-(3-(3,5-Difluorophenyl)propyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid

Procedure

The title compound was prepared from 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester (from EXAMPLE 1, Step I) and 4-(3-(3,5-difluorophenyl)propyl)piperidine.HCl (from EXAMPLE 95, Step E) using procedures analogous to those described in EXAMPLE 1, Steps J and K. For the title compound: 1H NMR (500 MHz, CD3OD) δ 1.14-1.47 (1OH). 1.58-1.68 (6H). 1.77-1.84 (6H). 2.06 (t, J=11.0, 1H), 2.36 (d, J=12.3, 1H), 2.53-2.59 (3H). 2.75-2.81 (2H). 2.96 (d, J=10.5, 1H), 3.11 (q, J=10.5, 1H), 3.30-3.42 (3H). 3.57-3.60 (2H). 6.67-6.72 (m, 1H). 6.74-6.76 (2H). 7.25-7.28 (m, 1H). 7.34-7.89 (4H); ESI-MS 539 (M+H).

Sources & evidence

ORD record
ord-4b64ee2f96de4a2da35e2a82c98160e6
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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