Hydrazine → cis-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentylamine

Participants

Reaction Steps

To a mixture of (±)-cis-2-[3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-isoindole-1,3-dione (1.03 g, 2.98 mmol) (from Example 10b supra) in ethanol/tetrahydrofuran (2:1, 20 mL) was added anhydrous hydrazine (1.2 mL, 38.90 mmol) (Aldrich). After stirring overnight the reaction mixture was filtered. The solids were washed with diethyl ether (approx. 30 mL) and the combined filtrate was concentrated. The residue was treated with diethyl ether again (approx. 30 mL) and the resulting mixture was filtered again and concentrated to give (±)-cis-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamine as a colorless oil. (Yield 570 mg, 88%).

Provenance & Evidence