Boron Trichloride → HCID 67089891, compound

Participants

Reaction Conditions

Reaction Steps

Cool a solution of N-{3-[4-((1R,3S)-1-aminomethyl-5-methoxy-6-methyl-isochroman-3-yl)-piperidin-1-yl]-1-methyl-propyl}-4-chloro-benzamide in anhydrous dichloromethane (4 mL) to −20° C., and add 6 equivalents of BCl3 (using 1M BCl3 in dichloromethane) slowly into the solution. Following complete addition, stir the reaction mixture at −20° C. for 2 hours and 0° C. for 1 hour. Cool again to −20° C. and quench with anhydrous CH3OH (0.5 mL). Allow the resulting solution to warm to room temperature and concentrate. Purify the crude product on a 2 g SCX column and then by chromatography on a 1 g silica gel column (eluted by 7N NH3 in methanol:ethyl acetate=1:10). Collect the appropriate fractions, concentrate and convert to the title compound with 2M HCl in diethyl ether. CIMS 486.2, tR (min)=2.30.

Provenance & Evidence