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

反応式

[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

参加物

反応物 2

HCID 4311764Sodium borohydride

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

生成物 1

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

実験手順

Following the procedure described for Preparation 8, 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, J=4.15 Hz, 1H), 1.75-1.40 (m, 5H); MS 252.2 (M+1).

後処理

customPurification by medium pressure chromatography

出典と根拠

ORDレコード: ord-d0da7fd5b4944ab8af3edcd387d67416
出典データセット: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06642266B2

反応ノート

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