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

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).

後処理

customPurification by medium pressure chromatography

出典と根拠

ORDレコード: ord-9fea32d3af9d4387822e46561c7d7f5c
出典データセット: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07192979B2

反応ノート

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