Ammonium Hydroxide → 9-tert-butyl-2-bromo-3-methoxy-5,6,9,10,11,12-hexahydro-8H-azepino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 1 g of 13a (prepared analogously to compound 3c, starting from 2-(tert-butyl(pent-4-ynyl)amino)-2-oxoacetic acid) and 1 g of sodium acetate in 10 ml of acetic anhydride was heated at 100° C. for 1 hr. The reaction mixture was cooled and 30 ml of water was added and stirred for 1 hr to decompose excess anhydride. The reaction mixture was neutralized by addition of cold conc. NH4OH and the product was extracted with ethyl acetate. The extract was washed with water, dried, concentrated and passed through a short silica column (toluene/ethyl acetate as eluent). The product obtained was triturated with heptane, to provide 0.65 g of 13b as white crystalline material; Mp 163-165° C. MS-ESI: [M+1] 417.13 and 419.17.

Provenance & Evidence