(+)-(1S,3S)-(3-azido-cyclopentyloxy)-tert-butyl-dimethyl-silane → (+/-)-trans-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentylamine

Participants

Reaction Steps

A mixture of (±)-trans-(3-azido-cyclopentyloxy)-tert-butyl-dimethyl-silane (400 mg, 1.66 mmol) (from Example 9b supra) and platinum oxide (38 mg, 0.17 mmol) (Aldrich) in ethanol (6 mL) was stirred under 1 atmosphere of hydrogen pressure for 2 hours. The reaction mixture was then filtered. The solids were washed with tetrahydrofuran (approx. 40 mL) and the combined organic layer was evaporated under reduced pressure to give (±)-trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamine as a colorless liquid. (Yield 270 mg, 76%).

Provenance & Evidence