4-[3-(4-Fluorophenyl)propyl]piperidine → 2-(R)-(3-(S)-((4-(3-(4-Fluorophenyl)propyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid

HRID 1386747Notes

Reaction equation

HRID 1386747 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]([CH2:25][CH:26]2[CH2:29][CH2:28][CH2:27]2)[C:15]([O:17]CC2C=CC=CC=2)=[O:16])[CH2:4]1)=O.[F:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][CH2:39][CH:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[CH:33][CH:32]=1>>[F:30][C:31]1[CH:32]=[CH:33][C:34]([CH2:37][CH2:38][CH2:39][CH:40]2[CH2:41][CH2:42][N:43]([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]([CH2:25][CH:26]4[CH2:29][CH2:28][CH2:27]4)[C:15]([OH:17])=[O:16])[CH2:4]3)[CH2:44][CH2:45]2)=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 30590224-[3-(4-Fluorophenyl)propyl]piperidine2×HCID 599245802-(R)-(3-(R)-Formyl-4-(S)-phenylpyrrolidin-1-yl)-3-(cyclobutyl)propionic acid, benzyl ester

Product 1

HCID 206723772-(R)-(3-(S)-((4-(3-(4-Fluorophenyl)propyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-3-(cyclobutyl)propanoic acidYield 85.5%

Procedure

The title compound was prepared from 25 mg (0.06 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, benzyl ester (from EXAMPLE 25, Step B) and 16 mg (0.06 mmol) of 4-(3-(4-fluorophenyl)propyl)piperidine.HCl (from EXAMPLE 96, Step B) using procedures analogous to those described in EXAMPLE 95, Steps F and G. 26 mg (81%) of the title compound was obtained: ESI-MS 507 (M+H); HPLC A: 2.69 min.

Sources & evidence

ORD record
ord-1706fae29608430fa05fcac4e4908774
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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