Benzyl Alcohol → HCID 68358820, compound

Participants

Reaction Steps

To a solution of (1R,3S)-3-cyano-2,2,3-trimethylcyclopentanecarboxylic acid (2.71 g, 14.95 mmol) in toluene (38.5 ml) and THF (4.27 ml) was added triethylamine (3.13 ml, 22.43 mmol) dropwise, followed by addition of diphenylphosphoryl azide (3.87 ml, 17.94 mmol). The reaction was stirred at room temperature for 1.5 hrs. Benzyl alcohol (1.866 ml, 17.94 mmol) was added. The reaction was heated at 110° C. for 2 hrs. The reaction was cool to room temperature, and diluted with ethyl acetate. The solution was washed successively with saturated sodium bicarbonate, water, and brine. The organic extract was dried with sodium sulfate, filtered, and concentrated under reduced pressure, yielding an orange oil. The oil was dissolved in 50% ethyl acetate/hexanes (5 ml) and loaded directly on a pre-packed silica gel column. The crude product was purified via medium pressure chromatography (0-50% EtOAc-hexanes solvent system over 20 minutes) to afford benzyl (1R,3S)-3-cyano-2,2,3-trimethylcyclopentylcarbamate (2.78 g, 9.71 mmol, 64.9% yield) as a colorless oil. ESI-MS m/z 287.2 ([M+H]+).

Provenance & Evidence