Benzyl Bromide → tert.-Butyl-[(2S)-1-(benzyloxy)-3-phenylpropan-2-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

500 mg (1.99 mmol) of N-Boc-L-phenylalaninol were dissolved in 5 ml DMF and cooled down to 0° C. under argon atmosphere. Then 159 mg (3.98 mmol) of a 60% suspension of sodium hydride was added in liquid paraffin. The reaction composition then was stirred until completion of gas formation and then mixed with 260 μl (2.19 mmol) of benzyl bromide. The cooling bath was removed and the reaction composition stirred for 2 hours at RT. Afterwards, the batch was evaporated, the residue absorbed in ice water and the composition extracted with dichlormethane. The organic phase was washed with saturated saline, dried over magnesium sulphate and evaporated. The residue was purified by means of a preparative HPLC. The yield was 226 mg (33% o. th.) of the title compound.

Provenance & Evidence