Boron Trichloride → HCID 67089985, compound

Participants

Reaction Conditions

Reaction Steps

Cool a solution of (1R,3S) [5-Isopropoxy-6-methyl-3-(1-phenethyl-piperidin-4-yl)-isochroman-1-ylmethyl]-methyl-amine 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 and concentrate the appropriate fractions and treat with 2M HCl in diethyl ether to obtain the title compound. CIMS 395.4 (MH+), tR (min)=2.17.

Provenance & Evidence