Hydrochloric Acid → 2-(3-(S)-((4-Hydroxy-4-(3-phenylpropyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)acetic acid, benzyl ester

HRID 1386675Notes

Reaction equation

HRID 1386675 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]([CH2:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:4]1)=O.[OH:25][C:26]1([CH2:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.Cl>>[OH:25][C:26]1([CH2:32][CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:31][CH2:30][N:29]([CH2:1][C@@H:3]2[C@@H:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:6][N:5]([CH2:14][C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:4]2)[CH2:28][CH2:27]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 4169034-(3-Phenylpropyl)piperidin-4-olHCID 1317227942-(3-(R)-Formyl-4-(S)-phenylpyrrolidin-1-yl)acetic acid, benzyl ester

Product 1

HCID 1317227932-(3-(S)-((4-Hydroxy-4-(3-phenylpropyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)acetic acid, benzyl esterYield 70%

Procedure

The title compound was prepared from 30 mg (0.094 mmol) of 2-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)acetic acid, benzyl ester (from EXAMPLE 8, Step C) and 28 mg (0.10 mmol) of 4-hydroxy-4-(3-phenylpropyl)-piperidine.HCl using a procedure analogous to that described in EXAMPLE 1, Step J to provide 34.5 mg (70%) of the title compound: RF: 0.26 (19:1 v/v CH2Cl2/MeOH); 1H NMR (300 MHz) δ 1.24-1.69 (m, 8H), 2.16-3.14 (m, 14H), 3.43 (ABq, J=16.8, 2H), 5.16 (ABq, J=12.2, 2H), 7.15-7.37 (m, 15H).

Sources & evidence

ORD record
ord-efad4ee9860b496085cdcd1d7f304f89
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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