Ammonia → {3-[({1-[(Methylamino)methyl]cyclopropyl}carbonyl)amino]propyl}(triphenyl)phosphonium bromide

Participants

Reaction Steps

(3-{[(1-{[(tert-butoxycarbonyl)(methyl)amino]methyl}cyclopropyl)carbonyl]amino}-propyl)(triphenyl)phosphonium bromide (809 mg, 1.32 mmol) was dissolved in methylene chloride (4.0 mL) and methanol (0.4 mL). The solution at room temperature was treated with 2.0 M hydrogen chloride in diethyl ether (1.7 mL, 3.44 mmol). The mixture was stirred overnight at room temperature. To the incomplete reaction was added additional 2.0 M hydrogen chloride in diethyl ether (0.36 mL, 0.71 mmol). After 3 additional hours, the reaction mixture was cooled with an ice bath and treated with 7N ammonia in methanol (0.77 mL, 5.42 mmol). After 30 minutes, the slurry that resulted was filtered, and the solids were washed with methylene chloride. The filtrate was concentrated to give the title compound (760 mg, 110%, 85% pure). The product of step 4 was used crude in next step.

Provenance & Evidence