Ammonia → N-Methyl-3-(((2R)-1-methyl-2-pyrrolidinyl)methyl)-1H-indole-5-methanesulfonamide

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Reaction Steps

A solution of (R)-N-Benzyl-1-[1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide (from step (f), 2.04 g) in tetrahydrofuran (2 ml) was added dropwise to liquid ammonia (10 ml) at −40° C. under a nitrogen atmosphere. Sodium (approximately 500 mg) was then added portionwise to the colourless solution, until a permanent dark blue coloured solution was obtained. The blue solution was stirred for a further 30 min at −40° C. before saturated ammonium chloride solution (5 ml) was added and the grey slurry warmed to ambient temperature over an 8 hr period. The white slurry was then diluted with water (10 ml), filtered and dried in vacuo at 50° C. to give the title compound (733 mg, 56%) as a white solid. m.p. 209-213° C.

Provenance & Evidence