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

HRID 352586Notes

Reaction equation

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

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 129700935-[4-(3-Fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one

Product 1

HCID 129700945-[4-(3-Fluoro-phenyl)-3-hydroxy-butyl]-pyrrolidin-2-oneYield 101.9%

Procedure

Analogous to the procedure described for Example 1A, Step B, 5-[4-(3-fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one (2.17 g, 8.71 mmol) was reduced with NaBH4 (165 mg, 4.35 mmol). Purification by medium pressure chromatography using a solvent gradient (1:1 hexanes:EtOAc to EtOAc to 1% MeOH in CH2Cl2 to 3% MeOH in CH2Cl2 to 6% MeOH in CH2Cl2) provided 5-[4-(3-fluoro-phenyl)-3-hydroxy-butyl]-pyrrolidin-2-one (2.23 g). 1H NMR (CDCl3) δ7.27 (m, 1H), 6.94 (m, 3H), 6.38 (m, 1H), 3.82 (m, 1H), 3.66 (m, 1H), 2.79 (m, 1H), 2.67 (m, 1H), 2.33-2.21 (m, 3H), 1.92 (d,1H), 1.75-1.40 (m, 5H); MS 252.2 (M+1).

Workup

customPurification by medium pressure chromatography

Sources & evidence

ORD record: ord-c803c8b1d44948b6a982ebe9269ef4e3
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06747054B2

Reaction notes

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