Triacetoxyperiodinane → methyl 14-cyclohexyl-7-oxo-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Participants

Reaction Steps

To a solution of methyl (7S)-14-cyclohexyl-7-hydroxy-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (from Step 3) in DCM (0.1 M) was added Dess-Martin periodinane (DMP, 1.2 eq), and the mixture was stirred for 1 h at RT. At this point another 0.6 eq of DMP were added and the reaction left overnight. The reaction mixture was diluted with EtOAc and washed with an aqueous solution of a 1:1 mixture containing sodium thiosulfate and NaHCO3 (both saturated solutions), then with water and brine. Drying over Na2SO4, filtration and concentration in vacuo gave the crude product, which was used without further purification (90%); MS (ES+) m/z 404 (M+H)+.

Provenance & Evidence