4-Methylmorpholine → HCID 54195888, compound

Participants

Reaction Steps

A solution of 2.44 g (6.44 mmol) of L-valine benzyl ester p-toluenesulfonate in 100 ml of dichloromethane was cooled under N2 atmosphere to 0° C. and treated sequentially with 1.15 g (6.44 mmol) of nicotinyl chloride hydrochloride and 2.8 ml (26 mmol) of 4 -methylmorpholine. After being stirred at ambient temperature overnight, the resulting solution was diluted with 200 ml of diethyl ether, washed sequentially with water, aqueous NaHCO3, and saturated brine, dried over Na2SO4, and concentrated in vacuo to give 2.09 g (95%) of the desired compound. 1H NMR (CDCl3) δ 0.96 (d, J=7 Hz, 3H), 1.01 (d, J=7 Hz, 3H), 2.30 (m, 1H), 4.83 (dd, J=9, 5 Hz, 1H), 5.20 (AA', 2H), 6.67 (br d, 1H), 7.37 (br s, 6H), 8.11 (dd, J=8, 2 Hz, 1H), 8.74 (br, 1H), 9.01 (s, 1H).

Provenance & Evidence