Benzyl Alcohol → HCID 68358820, compound

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]+).

1. temperatureThe reaction was heated at 110° C. for 2 hrs
2. temperatureThe reaction was cool to room temperature
3. washThe solution was washed successively with saturated sodium bicarbonate, water, and brine
4. extractionThe organic extract
5. dry with materialwas dried with sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customyielding an orange oil
9. customThe crude product was purified via medium pressure chromatography (0-50% EtOAc-hexanes solvent system over 20 minutes)

ORD record

ord-ab4e4dd5afbf4e90b20cf24ab012c374

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921368B2