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

HRID 458975노트

반응식

HRID 458975 반응식
[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

참가 물질

3

반응물 2

HCID 4311764Sodium borohydrideHCID 129700935-[4-(3-Fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one

생성물 1

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

실험 절차

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).

후처리

  1. customPurification by medium pressure chromatography

출처 및 근거

ORD 기록
ord-9fea32d3af9d4387822e46561c7d7f5c
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192979B2

반응 노트

불러오는 중…