Sodium Hydroxide → N-benzyl-2-{[(7S)-11-carboxy-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocin-7-yl]oxy}-N-methylethanaminium chloride

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Reaction Steps

To a suspension of methyl (7S)-14-cyclohexyl-7-hydroxy-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (prepared as described in International patent application publication WO2006/046030) in toluene (0.05 M), were added 10 eq. of 30% w/w aq. NaOH followed by 0.25 eq. of tetrabutylammonium bromide. After stirring for 30 min, 2.5 eq. of N-benzyl-2-chloro-N-methylethanaminium chloride were added, and the reaction mixture was stirred at 60° C. for 16 h. The reaction mixture was concentrated in vacuo, and the residue purified by RP-HPLC (WATERS XTERRA prep. C18 column, 5um, 19×100 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried in the presence of HCl to afford the title compound (25%) as a white powder. (ES+) m/z 539 (M+H)+.

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