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

HRID 1267431노트

반응식

HRID 1267431 반응식
[Cl: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+]>>[Cl: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 129700905-[4-(3-Chloro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one

생성물 1

HCID 129700915-[4-(3-Chloro-phenyl)-3-hydroxy-butyl]-pyrrolidin-2-one수율 79.9%

실험 절차

Analogous to the procedure described for Example 1A, Step B, 5-[4-(3-chloro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one (1.9 g, 7.15 mmol) was reduced with NaBH4 (135 mg, 3.57 mmol). Purification by medium pressure chromatography eluting with a solvent gradient (1:1 hexanes:EtOAc to EtOAc to 1% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2 to 8% MeOH in CH2Cl2) provided 5-[4-(3-chloro-phenyl)-3-hydroxy-butyl]-pyrrolidin-2-one (1.53 g). 1H NMR (CDCl3) δ7.22 (m, 3H), 7.07 (m, 1H), 6.51 (d, 1H), 3.82 (m, 1H), 3.66 (m, 1H), 2.77 (m, 1H), 2.66 (m, 1H), 2.33-2.19 (m, 3H), 2.04 (d, 1H), 1.74-1.45 (m, 5H); MS 268.2 (M+1).

후처리

  1. customPurification by medium pressure chromatography
  2. washeluting with a solvent gradient (1:1 hexanes:EtOAc to EtOAc to 1% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2 to 8% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-b7c7f9c08738471f95879419110c9025
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06552067B2

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