4-Methylmorpholine → HCID 86619280, compound

Participants

Reaction Steps

To a stirred solution of (1,2-trans)-2-[(cyclopropylmethyl)amino]cyclohexanol (117a) (4.34 g, 25.6 mmol) in THF (100 mL) was added potassium (2R,3S)-3-phenyloxirane-2-carboxylate (64a) (5.06 g, 25.0 mmol), HOBt (4.20 g, 27.4 mmol), NMM (8.25 mL, 75.0 mmol) and EDAC-HCl (5.94 g, 31.0 mmol). The mixture was stirred at ambient temperature under nitrogen overnight. The solvent was evaporated and the residue was purified by flash chromatography on silica gel eluting with dichloromethane ethyl acetate (3:1 then 1:1) followed by 10% methanol/dichloromethane to afford the title compound as a sticky white gum (5.22 g, 66%). The foam when dissolved in a little ether gave, on standing at RT overnight, a white solid (1.65 g, 21%), mp 110-120° C. TLC Rf˜0.50 (4:1 hexane:ether). 1H NMR (300 MHz, CDCl3) δ0.19-0.41 (m, 2H), 0.53-0.59 (m, 2H), 0.80-1.37 (m, 4H), 1.45-1.60 (m, 1H), 1.65-1.86 (m, 3H), 2.03-2.18 (m, 2H), 3.10-3.82 (m, 4H), 3.99-4.13 (m, 1H), 7.36 (m, 5H). HPLC (Method B): 3.67 min. On standing in the HPLC vial the 3.67 min peak diminished and a peak at 4.57 min (117c) increased.

Provenance & Evidence