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

HRID 2560

Reaction equation

HRID 2560 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f043af33bf7d4a64ba8d85518371337b
Source dataset
uspto-grants-1998_03
Patent number
US05728899

Linked notes

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