Hydrochloric Acid → 2,5,7-Triazaspiro[3.4]octan-8-one--hydrogen chloride (1/1)

Participants

Reaction Steps

To a solution of 2-benzhydryl-5-benzyl-2,5,7-triazaspiro[3.4]oct-6-en-8-one (I-3A-5a; 1.83 g, 4.80 mmol) in methanol/methylene chloride was added excess 1 M HCl in diethyl ether (10 ml). After stirring for 10 minutes, the solvent was removed, in vacuo, and the resultant hydrochloride salt dissolved in methanol (50 ml). After the addition of 20% Pd(OH)2 on carbon (50% water; 1.1 g), the mixture was placed on a Parr® shaker and then reduced (50 psi H2) at room temperature for 22 hours. The reaction was filtered through a 0.45 μM disk, and then concentrated, in vacuo, to give a gummy solid. This material was triturated from methanol to afford I-3A-5b (450 mg, 47%) as a tan solid: +APcI MS (M+1) 127.9; 1H NMR (400 MHz, CD3OD) δ 4.51 (s, 2H), 4.41-4.33 (m, 4H).

Provenance & Evidence