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

HRID 2219680Notes

Reaction equation

HRID 2219680 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 Compound 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) δ 7.42 (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-ab119f720f73487ea4a3b2849bbe920d
Source dataset
uspto-grants-2008_08
Patent number
US07414071B2

Reaction notes

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