Sodium Hydroxide → 7-({2-[benzyl(methyl)amino]ethoxy}methyl)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of (+)-methyl 14-cyclohexyl-7-(hydroxymethyl)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (second eluting isomer) in toluene (0.04 M) was treated with 30% w/v NaOH (10 eq) and tetrabutylammonium bromide (0.25 eq) followed by N-benzyl-2-chloro-N-methylethanaminium chloride (prepared as described in example 7 step 1) (2.5 eq). The resulting solution was stirred at 65° C. for 18 h. Toluene was removed in vacuo, the residue was taken up in EtOAc and washed with 1N HCl (aq) and brine before drying (Na2SO4), filtering and concentrating in vacuo to afford the product as an oil that was used without further purification. (ES+) m/z 553 (M+H)+.

Provenance & Evidence