Diisopropylamine → HCID 11119047, compound

Participants

Reaction Conditions

Reaction Steps

A solution of diisopropylamine (35 ml, 250 mmol) in anhydrous tetrahydrofuran (275 ml) is treated dropwise at 0° C., under argon, with n-butyllithium (2.5 M in hexane, 100 ml, 250 mmol). The resulting mixture is agitated at 0° C. for 15 min, then cooled down to −78° C. and treated with tert-butyl acetate (33.8 ml, 250 mmol). After agitation at −78° C. for 15 min, the resulting lithiated reagent is added dropwise, over 1 hour, using a transfer canula, to a solution of 1-(2-oxo-1,2-dihydro-4-pyridinyl)-1-propanone (obtained according to 1.g, 15.2 g, 100 mmol) at −78° C. in anhydrous tetrahydrofuran (330 ml) and the resulting mixture is maintained at −78° C. for 15 min, then allowed to return to 0° C. for 1 hour. The reaction medium is hydrolyzed by the addition of water (60 ml) then the volatiles are evaporated off under reduced pressure. The residue is taken up in ethyl acetate and the resulting solution is washed with water, dried and concentrated. The residue is suspended in diethyl ether and filtered in order to produce after drying 21.5 g (80%) of a white solid, m.p. 167° C.

Provenance & Evidence