Dimethyl Carbonate → HCID 21912726, compound

Participants

Reaction Steps

A solution of 0.51 g (2.1 mmol) of 4-propionyl-1-(tert-butoxycarbonyl)piperidine (from Step A) and 0.35 mL (17.6 mmol) of dimethylcarbonate in 5 mL of tert-butyl, methylether at 0° C. was treated with 0.45 g (4.0 mmol) of potassium tert-butoxide. After 10 minutes at 0° C., the reaction was stirred at rt for 17 hours and refluxed for 3 hours. The reaction was quenched with 1 N HCl and partitioned between 100 mL of Et2O and 100 mL of 1 N HCl. After separating phases, the organic layer was washed with 100 mL of brine, dried over MgSO4 and concentrated. The residue was purified with a 40M Biotage column using 9:1 v/v of hexanes/acetone as the eluant to afford the title compound as a straw colored oil: RF: 0.32 (4:1 v/v hexanes/acetone); 1H-NMR (500 MHz) δ 1.35 (d, J=7.1, 3H), 1.42–1.66 (m, 11H), 1.79–1.80 (m, 2H), 2.68–2.79 (m, 3H), 3.71 (q, J=7.1, 1H), 3.73, 3.77 (2s, 3H), 4.12 (m, 2H).

Provenance & Evidence