Toluene → HCID 67797504, compound

Participants

Reaction Conditions

Reaction Steps

(±)-Methyl-4-acetamido-1-cyclopentene-1-carboxylate (3.66 g, 20.0 mmol) was dried by evaporation of toluene giving a solution with a final volume of 50 mL. This solution was cooled to -70° C. under nitrogen. A solution of diisobutylaluminum hydride in toluene (1.5 M, 42 mL, 63 mmol) was added dropwise over 2 hours. The resulting hazy solution was stirred at -70° C. for an additional 40 minutes. Cold methanol (5 mL) was added dropwise, followed by a solution of sodium potassium tartrate (11.29 g) in water (15 mL) with the temperature maintained at -70° C. The resulting mixture was allowed to stir at 0° C. for several hours, diluted with methanol (150 mL) and filtered. The methanol was evaporated and the residual brown oil (3.44 g) chromatographed on silica gel. Title compound was eluted as pale yellow oil with 5% methanol-chloroform; 1.30 g (42%).

Provenance & Evidence