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

HRID 478874Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.[BH4-].[Na+]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([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:6][CH:7]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride2×

HCID 227125185-[4-(4-Fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one

Product 1

HCID 227124475-(4-(4-Fluoro-phenyl)-3-hydroxy-butyl)-pyrrolidin-2-oneYield 75.5%

Procedure

Following the procedure described for Preparation 8, Step B, 5-[4-(4-fluoro-phenyl)-3-oxo-butyl ]-pyrrolidin-2-one (2.64 g, mmol) was reduced with NaBH4 (400 mg, mmol) at room temperature for 1 h. Additional NaBH4 (150 mg) was added and the reaction was stirred for 20 h. Purification by medium pressure chromatography using a solvent gradient (CH2Cl2 to 2% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2) provided 5-[4-(4-fluoro-phenyl)-3-hydroxy-butyl]-pyrrolidin-2-one (2.01 g). 1H NMR (CDCl3) δ7.14 (m, 2H), 6.98 (m, 2H), 6.78 (m, 1H), 3.76 (m, 1H), 3.65 (m, 1H), 2.76 (m, 1H), 2.64 (m, 1H), 2.32-2.18 (m, 4H), 1.72-1.47 (m, 5H).

Workup

customPurification by medium pressure chromatography

Sources & evidence

ORD record: ord-339c2bc515714eb0a67a4e173d8451c0
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642266B2

Reaction notes

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