Hydrochloric Acid → 2-(R)-(3-(S)-((4-(3-Phenylpropyl)piperidin-1-yl)methyl)-4 (S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, benzyl ester

HRID 1386704Notes

Reaction equation

HRID 1386704 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C@@H:17]3[C@@H:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=4)[CH2:20][N:19]([C@H:29]([CH2:33][CH:34]4[CH2:37][CH2:36][CH2:35]4)[C:30]([OH:32])=[O:31])[CH2:18]3)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:38]1([CH2:44]CCC2CCNCC2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.Cl>>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][C@@H:17]3[C@@H:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=4)[CH2:20][N:19]([C@H:29]([CH2:33][CH:34]4[CH2:35][CH2:36][CH2:37]4)[C:30]([O:32][CH2:44][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[O:31])[CH2:18]3)[CH2:14][CH2:15]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 876784-(3-Phenylpropyl)piperidineHCID 20672386(R)-3-Cyclobutyl-2-{(S)-3-(3-fluoro-phenyl)-4-[4-(3-phenyl-propyl)-piperidin-1-ylmethyl]-pyrrolidin-1-yl}-propionic acid

Product 1

HCID 1317228052-(R)-(3-(S)-((4-(3-Phenylpropyl)piperidin-1-yl)methyl)-4 (S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, benzyl esterYield 102.1%

Procedure

The title compound was prepared from 23.2 mg (0.052 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, benzyl ester (from EXAMPLE 26, Step A) and 12.8 mg (0.052 mmol) of 4-(3-phenylpropyl)piperidine.HCl using a procedure analogous to that described in EXAMPLE 1, Step J to provide 31.7 mg (96%) of the title compound: RF: 0.57 (1:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 1.13-3.27 (m, 33H), 5.14 (s, 2H), 6.86-6.99 (m, 3H), 7.14-7.38 (m, 11H).

Sources & evidence

ORD record
ord-6bb0f63b66344746b5f41e691ee740ef
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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