N-methoxy-N-methylpentanamide → 1-[2-(t-Butoxycarbonylamino)pyridin-3-yl]hexan-2-one

Participants

Reaction Steps

A solution of 2-(t-butoxycarbonylamino)-3-methylpyridine (X) (5.3 g) (prepared, e.g., as described in Preparation 17), in tetrahydrofuran (100 ml) was cooled to -50° C. and a solution of sec-butyllithium (46 ml of 1.3M in cyclohexane) was added. After 10 minutes, the dark solution was treated with N-methoxy-N-methylvaleramide (4.4 g) and the resulting solution was stirred 10 minutes. The mixture was diluted with ether, washed with water, dried over sodium sulfate and evaporated. Crystallization of the residue from hexane afforded 1-[2-(t-butoxycarbonylamino)pyridin-3-yl]hexan-2-one (4.3 g), a compound of Formula (Y), as a white solid m.p. 66°-67° C.

Provenance & Evidence