Water → HCID 137331230, compound

Participants

Reaction Steps

To a 0° C. solution of (±)-(4R*5R*)-5-{(1R*)-3-[3-(2,5-dimethylpyrrolyl)phenyl]-1-hydroxyprop-2-ynyl}-1-methyl-4-phenylpyrrolidin-2-one (prepared according to the procedure described for Example 8, 0.15 g, 0.37 mmol) and 2,6-lutidine (0.1 mL, 0.93 mmol) in CH2Cl2 (10 mL) was added TBDMSOTf (0.13 mL, 0.55 mmol). The reaction mixture was stirred for 2 h, allowed to warm to room temperature and treated with water. The resulting mixture was extracted with CH2Cl2, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography (80% EtOAc/hex) to give (±)-(4R*,5R*)-5-{(1R*)3-[3-(2,5-dimethylpyrrolyl)phenyl]-1-tert-butyldimethyl-silyloxyprop-2-ynyl}-1-methyl-4-phenylpyrrolidin-2-one (90 mg, 47%): mp 156-158° C.; TLC (50% EtOAc/hex) Rf 0.41.

Provenance & Evidence