Dimethylformamide → HCID 19868624, compound

Participants

Reaction Conditions

Reaction Steps

Combine N-(tert.-butyloxycarbonyl)-glycine (8.8 g), 1,1'-carbonyldiimidazole (8.1 g), and N,N-dimethylformamide (40 ml) at 10° C., and, after 10 min., add 8,10-bis(acetyloxy)-1,2,3,4-tetrahydro-11-methyl-6H-benzo[b]quinolizin-6-one (2.45 g) in N,N-dimethylformamide (40 ml) followed by 4-dimethylaminopyridine (6.1 g). Stir the reaction mixture at 25° C. overnight. Dilute the reaction mixture with water (250 ml) and extract with ethyl acetate. Combine the organic extracts, and wash them sequentially with water, saturated sodium bicarbonate solution, water, 5% aqueous acetic acid, and with water. Concentrate the dried, filtered ethyl acetate solution to give a residue. Chromatograph the residue over silica gel, and elute the column with 1°-2% methanol in dichloromethane. Combine fractions to give 8,10bis[(aminoacetyl)oxy]-11-methyl-1,2,3,4-tetrahydro-6H-benzo[b]quinolizine-6-one, m.p. 163°-164° C. (from MeOH-CH2Cl2). Use this material directly in the next step.

Provenance & Evidence