Acetic Acid → HCID 90008749, compound

Participants

Reaction Steps

To a stirring solution of 2-(propene-3-yl)cyclopentanone (0.745 g, 6.0 mmol) in 2,2,2-trifluoroethanol (5 mL) under an atmosphere of nitrogen was added (S)-α-methylbenzylamine (3.1 mL, 24 mmol), glacial acetic acid (1.38 mL, 24 mmol), and t-butylisonitrile (2.04 mL, 18 mmol). After stirring at room temperature for five days and then at 60° C. for an additional 2 days, the mixture was concentrated in vacuo, taken up in water (50 mL) and extracted using ethyl acetate (75 mL, then 50 mL). The combined organic layer was washed with brine (75 mL), dried using MgSO4, and concentrated in vacuo. The residual oil was dissolved in minimum quantity of methylene chloride prior to loading of the crude onto a silica gel column (175 mL). The crude mixture was purified by eluting the column with 20% ethyl acetate/heptane and then using a solvent mixture comprising 30% ethyl acetate/heptane to afford the subject compound single enantiomer (0.341 g, 15%) as a pale yellow viscous oil. NMR (CDCl3): δ 7.46 (m, 2 H), 7.31 (m, 2 H), 7.19 (m, 1 H), 6.27 (m, 1 H), 5.67 (m, 1 H), 4.90 (m, 2 H), 4.80 (br s, 1 H), 2.88 (m, 1 H), 2.43 (m, 2 H), 1.87 (m, 2 H), 1.50-1.80 (m, 10 H), 1.30 (s, 9 H). MS (M+1): 371.1; MS (M+Na): 393.4.

Provenance & Evidence