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

HRID 352579Notes

Reaction equation

HRID 352579 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-dfcb8f7956c4450e9eaec314853daae8
Source dataset
uspto-grants-2004_06
Patent number
US06747054B2

Reaction notes

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