Tetrahydrofuran → [4-(Cyclopentyloxy)phenyl]methanamine

Participants

Reaction Steps

Add a solution of 1M BH3-THF complex in THF (4.8 mL, 4.8 mmol) to neat 4-cyclopentyloxy-benzonitrile (300 mg, 1.6 mmol) and stir the mixture for 3 h at room temperature and then for 3 h at reflux. Cool to room temperature, pour the reaction into 2N aqueous HCl (10 mL) and stir the mixture for 1 h at room temperature then concentrate in vacuo. Dissolve the crude mixture in methanol and filter through SCX column eluting with methanol followed by 3M ammonia in methanol to obtain the title compound (223 mg, 73%).

Provenance & Evidence