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

Participants

Reaction Conditions

Reaction Steps

HOAc (cat.) was added to a stirred mixture of methyl (7R)-14-cyclohexyl-7-(methylamino)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (prepared as described in Example 1, Step 5) (0.03 M) and chloroacetaldehyde (50 wt % in water; 1.5 eq) in MeOH. NaCNBH3 (1.5 eq) was introduced and the reaction heated at 60° C. for 2 h. The reaction was allowed to cool to RT and partitioned between water and EtOAc. The organics were washed with saturated NaHCO3 (aq), brine before being dried (Na2SO4) filtered and concentrated in vacuo. The material was taken on without further purification. (ES+) m/z 480 (M+H)+; 482 (M+H)+.

Provenance & Evidence