4-Methylmorpholine → HCID 940643, compound

Participants

Reaction Steps

N-Morpholinecarbonyl-L-aline methyl ester: HCL-Valine methyl ester (25 g) was dissolved under argon in 600 mL of freshly distilled THF and 100 mL of dry DMF and 1.0 equivalents of N-methyl morpholine. The resulting solution was cooled to -15° and an additional 1.1 equivalent of N-methyl morpholine followed by 1.1 equivalents of morpholine chloride was added. The reaction was allowed to come slowly to room temperature and stir overnight. The reaction is then poured into 300 mL of 1N HCL and extracted with ethyl acetate (2×200 mL). The combined organic fractions were washed with 1N HCL (50 mL), brine (50 mL), dried over MgSO4, filtered and the solvents were removed under reduced pressure to give 33 g of N-morpholinecarbonyl-valine methyl ester as a white solid: NMR (100 MHz, CDCl3 δ 0.9 (dd, 6), 2.1 (septet, 1), 3.0 and 3.65 (morpoline triplets, 4 and 4), 4.98 (N-H).

Provenance & Evidence