Acetic Acid → HCID 117953322, compound

Participants

Reaction Steps

To a round bottom flask containing 2-(propene-3-yl)cyclopentanone (0.745 g, 6.0 mmol) was added a premixed slurry of 8 N methylamine/ethanol (3.0 mL, 24 mmol) and glacial acetic acid (1.37 mL, 24 mmol) in trifluoroethanol (3 mL). The reaction mixture is stirred for 30 minutes and then treated with t-butylisonitrile (2.04 mL, 18 mmol). After stirring for 2 days, the reaction mixture is diluted with methylene chloride (10 mL), and chromatographed using a silica gel column (175 mL). A gradient elution using 20%, 50%, and 80% mixture of ethyl acetate and heptane afforded the subject compound (559 mg, 33%) as a white crystalline solid. NMR (CDCl3): δ 5.82 (br s, 1H), 5.70 (m, 1H), 4.90-5.00 (m, 2H), 2.96 (s, 3H), 2.63 (m, 1H), 2.37 (m, 1H), 2.26 (m, 1H), 2.04 (s, 3H), 1.60-1.85 (m, 4H), 1.40-1.60 (m, 2H), 1.24 (s, 9H). MS (M+1): 281.4; MS (M+Na): 303.4.

Provenance & Evidence