Benzyl Alcohol → HCID 86707712, compound

Participants

Reaction Steps

Triethylamine (1.795 ml, 12.88 mmol) was added dropwise to a solution of (1R,3S)-3-(methoxycarbonyl)-2,2,3-trimethylcyclopentanecarboxylic acid (1.84 g, 8.59 mmol) in toluene (22.08 ml) and THF (2.454 ml), followed by addition of diphenylphosphoryl azide (2.221 ml, 10.31 mmol). The reaction was stirred at room temperature for 1.5 hours. Benzyl alcohol (1.339 ml, 12.88 mmol) was added. The reaction was heated at 110° C. for 6 hrs. The reaction was cooled to room temperature and diluted with ethyl acetate. The solution was washed successively with (sat.) sodium bicarbonate, water, and (sat.) sodium chloride. The organic extract was dried with sodium sulfate, filtered, and concentrated under reduced pressure to give an orange oil. The crude product was chromatographed on the silica gel column eluted with 0-50% ethyl acetate in hexane to afford the title compound (1.74 g, 5.45 mmol, 63.4% yield) as a colorless oil. LC/MS found [M+H]+=320.1. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.39-7.27 (m, 5H), 5.15-5.01 (m, 2H), 4.14-4.02 (m, 1H), 3.70-3.62 (m, 3H), 2.53-2.40 (m, 1H), 2.20-2.08 (m, 1H), 1.51-1.40 (m, 2H), 1.22-1.19 (m, 3H), 1.05 (s, 3H), 0.73 (s, 3H).

Provenance & Evidence