Methanol → HCID 20069026, compound

Participants

Reaction Steps

A suspension of 44.1 mg. (0.159 mmol) of 6-methoxy-4-phenyl-2,3,4,5-tetrahydro-1H-benzo[e]isoindole hydrochloride, from Step 6, in 2 mL of methylene chloride is cooled to -78° C. and 0.64 mL of a 1M solution of boron tribromide in methylene chloride is added. The reaction is warmed to ambient temperature for 1 h and recooled to -78° C. before 1 mL of methanol is added. After warming to ambient temperature for 1 h, the solvents are removed in vacuo. Additional methanol (5 mL) is added and removed in vacuo. The product is chromatographed on silica gel, eluting with 18:1:1 ethyl acetate:formic acid: water to give 6-hydroxy-4-phenyl-2,3,4,5-tetrahydro-1H-benzo[e]isoindole formic acid salt.

Provenance & Evidence