Monobenzone → (S)-2-(4-Benzyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a slurry of NaH (562 mg, 8.44 mmol, 60% dispersion in mineral oil) in anhydrous DMF (5 mL) at 0° C. was added p-benzyloxy phenol (1.41 g, 7.0 mmol) in anhydrous DMF (5 mL) dropwise over 30 min under N2 atmosphere. The resulting slurry was stirred at 0° C. for 30 minutes, warmed to ambient temperature and stirred for 1 h before a solution of (S)-2-(Toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (2.5 g, 7.0 mmol) in DMF (10 mL) was added dropwise over 30 min at 0° C. The subsequent mixture was stirred at 85° C. 16 h. The reaction mixture was poured over ice-water, precipitated yellow solid was removed by filtration, washed with water and dried under reduced pressure. The crude product was crystallized from ether/hexane to obtain the title compound (1.2 g, 44%).

Provenance & Evidence