Water → (R)-tert-butyl 2-((S)-(3-chlorophenyl)(2-(methoxycarbonylamino)ethoxy)methyl)morpholine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-tert-butyl 2-((S)-(2-aminoethoxy)(3-chlorophenyl)methyl)morpholine-4-carboxylate (1.62 g, 4.38 mmol) and DMAP (280 mg) in dry CH2Cl2 (15 mL), Et3N (1.33 g, 13.14 mmol) was added. The resulting mixture was cooled to 0-5° C. in an ice-water bath and a solution of methyl chloroformate (2.06 g, 21.9 mmol) in dry CH2Cl2 (5 mL) was added dropwise. The reaction mixture was stirred for 1-2 h at 0-5° C. Tlc showed the starting material had disappeared. Water (30 mL) was added and the aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with 10% aq citric acid (2×10 mL) and brine, dried over Na2SO4, filtered and concentrated to the crude product, which was purified by preparative HPLC to afford the desired product (120 mg, 6%). 1H NMR (MeOD) 1.45 (s, 9H), 2.80-2.92 (m, 2H), 3.0 (m, 1H), 3.60 (s, 3H), 4.15 (m, 2H), 4.25 (d, 1H), 7.20-7.35 (m, 4H).

Provenance & Evidence