Methanol → HCID 53747152, compound

Participants

Reaction Steps

A solution of (+/-)-4-amino-3-(3 cyclopentyloxy-4-methoxyphenyl)-1-phenyl-1-butyne (50 mg, 0.15 mmol) and Et3N (0.2 ml) in EtOAc (30 ml) at 5° was treated with Ac2O (0.2 ml). After 5 minutes, the reaction was treated with MeOH, to decompose excess Ac2O. The reaction was washed with H2O and 0.05 N HCl, dried, and the solvent was evaporated. The residue was purified by flash chromatography (alumina, neutral, activity 1, 5% MeOH/CHCl3), and then by recrystallization from a mixture of cyclohexane and Et2O, and gave the titled compound, 37 mg (65%). mp 114-117°. 1H NMR (400 MHz, CDCl3) δ 7.42 (m, 2 H), 7.32 (m, 3 H), 6.92 (m, 2 H), 6.84 (d, 1 H), 5.78 (broad s, 1 H), 4.76 (m, lH), 4.02 (t, 1 H), 3.82 (s, 3 H), 3.64 (m, 1 H), 3.50 (m, 1 H), 2.06 (s, 3 H), 1.78-2.00 (m, 6 H), 1.62 (m, 2 H).

Provenance & Evidence