Ammonia → 4-Allyl-4-amino-adamantan-1-ol

Participants

Reaction Steps

5-Hydroxy-2-adamantanone (3.0 g, 18.1 mmol) was dissolved in a solution of ammonia in methanol (7N, 26 mL, 180 mmol, 10 eq.) and stirred for 15 min at room temperature. Then, 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane (5.4 mL, 28.9 mmol, 1.6 eq.) was added dropwise. The reaction mixture was stirred for 16 h at room temperature before the volatiles were removed in vacuo. The residue was taken up in methanol twice and evaporated, then lyophilized from water to give 4-allyl-4-amino-adamantan-1-ol (3) as a mixture of diastereomers. Rt=1.05 min, 1.79 min (Method 2). Detected mass: 270.3 (M+H+).

Provenance & Evidence