Boron tribromide → HCID 18643845, compound

Participants

Reaction Steps

A solution of 0.34 g (1.2 mmol) of [1R,8S,9aR] 1-amino-5-methoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene, from Step 7, in 9 mL of methylene chloride is treated with 4.4 mL (4.4 mmol) of a 1M solution of boron tribromide in methylene chloride, added dropwise at -78° C. The reaction is warmed to ambient temperature for 1 hour and recooled to -78° C. and the reaction is quenched with 5 mL of methanol. The reaction mixture is allowed to warm to ambient temperature and stirred for 1 hour. The solvent is removed in vacuo and 5 mL of methanol is added and the solution is concentrated to remove methyl borate by azeotropic distillation to give the title compound.

Provenance & Evidence