Reaction #2661

Reaction equation

(+/-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol

hydrogen

→

title compound

Yield 92.0%

(+/-)-cis-3-tert-butyldimethylsilyloxycyclopentanol

Yield 92.0%

Solvents

methanol

methanol

Conditions

Workup

1. 1
   Filtrationfilter through diatomaceous earth
2. 2
   Washrinse the solids with methanol (50 mL)
3. 3
   ConcentrationConcentrate the filtrate under vacuum (15 mmHg/40° C.)
4. 4
   Otherpurify the residue
5. 5
   workup.DISTILLATIONby Kugelrohr distillation (0.6 mmHg/60°-65° C.)

Procedure

Combine (+/-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (2.50 g, 11.6 mmol, prepared in example 3) and Ni2B (8.5 mL of a 0.14M slurry in methanol, 10 mol %) in methanol (14 mL). Stir the slurry under an atmosphere of hydrogen for 18.5 hours. Then replace the hydrogen atmosphere with nitrogen, filter through diatomaceous earth and rinse the solids with methanol (50 mL). Concentrate the filtrate under vacuum (15 mmHg/40° C.) and purify the residue by Kugelrohr distillation (0.6 mmHg/60°-65° C.) to provide the title compound as a colorless oil (2.31 g, 92%).

Source