m-Xylyl bromide → HCID 53993375, compound

Participants

Reaction Steps

To a cold (−78° C.) solution of methyl N-tert-butoxycarbonyl-piperidine-4-carboxylate (5.0 g, 20.5 mmol; Example 3, Step B) in anhydrous THF (70 mL), a solution of sodium bis(trimethylsilyl)amide (20.5 mL, 1M, 20.5 mmol) was added over a period of 30 min. The resultant mixture was stirred at −78° C. for 1 h., and 3-methylbenzyl bromide (2.77 mL, 20.5 mmol) was added. The reacting mixture was allowed to warm up to room temp. and stirred overnight. The product mixture was concentrated, and the residue was partitioned 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 10% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the title compound.

Provenance & Evidence