Trimethyl orthoformate → HCID 67344869, compound

Participants

Reaction Steps

Methyl (7R)-7-amino-14-cyclohexyl-3-(pyridin-2-ylmethoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate was dissolved in HC(OMe)3 (50 eq) and a solution of tert-butyl methyl(2-oxoethyl)carbamate (1.6 eq, prepared according to Tetrahedron 2002, 58, 1719-1737) in HC(OMe)3 (50 eq) was added. The mixture was stirred overnight at RT to allow formation of the imine. All volatiles were evaporated and the residual material was dissolved in MeOH/HOAc (0.05 M). NaCNBH3 (1 eq) was added and the mixture was stirred at RT for 1 h. Some formation of the N-formyl product was observed alongside formation of the desired product. The solution was used directly in the next step. (ES+) m/z 669 (M+H)+.

Provenance & Evidence