Methylamine → N-(1-Adamantylmethyl)-5-bromo-2-{[(2S)-2-hydroxy-3-(methylamino)propyl]oxy}isonicotinamide

Participants

Reaction Steps

A mixture of N-(1-adamantylmethyl)-5-bromo-2-[(2S)-oxiran-2-ylmethoxy]isonicotinamide (0.12 g) (Example 35(iii)), 40% aqueous methylamine (4 ml) and 1,4-dioxane (4 ml) was stirred for 4 hours. The reaction mixture was concentrated and the residue was purified by chromatography on silica gel eluting with ethyl acetate:ethanol:0.880 ammonia solution (4:1:0.1 to 1.5:1:0.1). The isolated material was dissolved in a solution of hydrogen chloride in 1,4-dioxane (10 ml of a 4M solution) and concentrated to afford the titled compound (0.039 g).

Provenance & Evidence