Sodium borohydride → tert-Butyl 3-hydroxycyclopentanecarboxylate

HRID 1367495노트

반응식

HRID 1367495 반응식
[C:1]([O:5][C:6]([CH:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([CH:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 14009986tert-Butyl 3-oxocyclopentane-1-carboxylate

생성물 1

HCID 14009988tert-Butyl 3-hydroxycyclopentanecarboxylate수율 67%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
2.5 °C

실험 절차

To a cold (ice bath) solution of Rac-3-Oxo-cyclopentanecarboxylic acid tert-butyl ester (1.43 g) in methanol (9 mL) was added sodium borohydride (0.293 g). The mixture was stirred 25 min at 0-5° C. then concentrated in vacuo. Ethyl acetate was added to the residue and the mixture was washed with water, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with dichloromethane/methanol (19:1 v/v) as eluant to afford the title compound (0.963 g, 67%) as colorless oil. MS (EI): 187.1 (M+H)+.

후처리

  1. concentrationthen concentrated in vacuo
  2. additionEthyl acetate was added to the residue
  3. washthe mixture was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel with dichloromethane/methanol (19:1 v/v) as eluant

출처 및 근거

ORD 기록
ord-725cfe38759e40028e982469be08d622
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893099B2

반응 노트

불러오는 중…