Triethylamine → (-)-cis-3-Acetoxy-cyclopentanol

HRID 2393902

반응식

HRID 2393902 반응식
[C:1]([O:4][C@@H:5]1[CH2:9][C@H:8]([OH:10])[CH:7]=[CH:6]1)(=[O:3])[CH3:2].C(N(CC)CC)C>C(O)C.[Ni]>[C:1]([O:4][C@@H:5]1[CH2:6][CH2:7][C@H:8]([OH:10])[CH2:9]1)(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 8471TriethylamineHCID 10154103rac-(1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate

생성물 1

HCID 15407441(-)-cis-3-Acetoxy-cyclopentanol수율 87.3%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

실험 절차

Dissolve (-)-cis-4-acetoxy-cyclopent-2-enol (11.0 g, 77.4 mmol, prepared in example 19) in ethanol (50 mL) and treat with Raney nickel (1.1 g, previously washed with water (2×50 mL) and ethanol (2×50 mL), Ra--Ni). Charge the atmosphere with hydrogen at 50 psi (344.74 kPa) and shake the mixture. After 20 minutes, filter the solution and treat the filtrate with triethylamine (1.0 mL, 7.2 mmol). After one hour concentrate the solution under vacuum and distill the residue by Kugelrohr distillation (60°-80° C., 1 mm Hg), to provide the title compound (9.74 g, 87%) as a colorless oil.

후처리

  1. washpreviously washed with water (2×50 mL) and ethanol (2×50 mL), Ra
  2. additionCharge the atmosphere with hydrogen at 50 psi (344.74 kPa) and shake the mixture
  3. filtrationfilter the solution
  4. concentrationAfter one hour concentrate the solution under vacuum
  5. distillationdistill the residue
  6. distillationby Kugelrohr distillation (60°-80° C., 1 mm Hg)

출처 및 근거

ORD 기록
ord-d9675e961a5e49c6812052f4306108f6
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05808112

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