Sodium Acetate → 9-tert-butyl-3-methoxy-2-bromo-14-(1,3-thiazol-5-yl)-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 220 mg of 17h and 150 mg of sodium acetate in 15 ml of acetic anhydride was stirred at 105° C. for 45 min. The reaction mixture was cooled, diluted with 60 ml of water and stirred at ambient temperature for 1 hr to destroy excess anhydride. The aqueous material was then neutralized by careful addition of cold con. aq. NH4OH. The product was extracted with ethyl acetate. The extract was washed with water, dried, concentrated and the material isolated was chromatographed over silica gel using a gradient of heptane/ethyl acetate as eluent. The material isolated was treated with ether/heptane, to give 85 mg of 17i as white crystals. MS-ESI: [M+1] 514.11 and 516.11.

Provenance & Evidence