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

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.

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)

ORD record

ord-f043af33bf7d4a64ba8d85518371337b

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05728899