Sodium borohydride → 5-[3-Hydroxy-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one

HRID 458968Notes

Reaction equation

HRID 458968 reaction equation
[O:1]=[C:2]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)[CH2:3][CH2:4][CH:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1.[BH4-].[Na+]>>[OH:1][CH:2]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=1)[CH2:3][CH2:4][CH:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 129700875-[3-Oxo-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one

Product 1

HCID 129700885-[3-Hydroxy-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-oneYield 86%

Procedure

Analogous to the procedure described for Example 1A, Step B, 5-[3-oxo-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one (1.37 g, 4.59 mmol) was reduced with NaBH4 (174 mg) at 0° C. over 2 h. Purification by medium pressure chromatography (2% MeOH in CH2Cl2) provided 5-[3-hydroxy-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one (1.19 g). 1H NMR (CDCl3) δ7.42 (m, 4H), 6.26 (m, 1H), 3.82 (m, 1H), 3.65 (m, 1H), 2.84 (m, 1H), 2.72 (m, 1H), 2.27 (m, 3H), 1.86 (m, 1H), 1.75–1.42 (m, 5H); MS 302.2 (M+1).

Workup

  1. customPurification by medium pressure chromatography (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c8f357a9b9004ef48256e993de7120a6
Source dataset
uspto-grants-2007_03
Patent number
US07192979B2

Reaction notes

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