alpha-Bromo-2-nitrotoluene → HCID 54074348, compound

Participants

Reaction Steps

To a cold (−78° C.) solution of ethyl N-tert-butoxycarbonylpiperidine-4-carboxylate (7.5 g, 29 mmol) in anhydrous THF (75 mL), a solution of sodium bis(trimethylsilyl)amide (40 mL, 1M, 40 mmol) was added over a period of 30 min. The resultant mixture was stirred at −78° C. for 1 h., and a solution of 2-nitrobenzyl bromide (7.6 g, 35) in THF (10 mL) was added. The reacting mixture was allowed to warm up to room temp. and stirred overnight. The product mixture was concentrated, and the residue partition between water and ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 20% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the title compound.

Provenance & Evidence