Methyl 2-(bromomethyl)benzoate → HCID 57941519, compound

Participants

Reaction Steps

A solution of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 300 mg, 1.5 mmol) and methyl 2-bromomethyl-benzoate (370 mg, 1.6 mmol) in dimethylformamide (15 mL) was heated at ˜100° C. for 2 days. The reaction mixture was allowed to cool and the solvent was evaporated. The residue was taken up in dichloromethane and purified on a Biotage 40S system, eluting with 0-2% methanol/dichloromethane to give 2-((4S,7R)-1,7,8,8-tetramethyl-3-oxo-1,3,4,5,6,7-hexahydro-4,7-methano-indazol-2-ylmethyl)-benzoic acid methyl ester (304 mg, 59%) as an orange oil. 1H NMR indicated that it contained minor impurities. It was used in the next step without further purification.

Provenance & Evidence