Tetrahydrofuran → methyl (7R)-7-azido-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of the foregoing product from step 1 in dry THF (0.06 M) azidotrimethylsilane (3.5 eq.) and tetrabutylammonium triphenyldifluorosilicate (3.5 eq.) were added. The reaction was stirred for 20 h at 65° C. then 1 more eq. of azidotrimethylsilane was added and the mixture stirred at 65° C. for 36 h. The volatiles were evaporated in vacuo and the crude dissolved in EtOAc was washed with hydrochloric acid (1 N), sodium hydrogen carbonate (saturated solutions) and brine. Drying over Na2SO4, filtration and concentration in vacuo gave the crude product, which was purified by flash chromatography on silica gel (5:95 EtOAc/PE) to afford the title compound as white foam (84%); MS (ES+) m/z 431 (M+H)+.

Provenance & Evidence