Triphenylphosphine → HCID 117634603, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S)-2-{[(benzyloxy)carbonyl]amino}-3-methoxypropyl methanesulfonate (37.6 g, 0.118 mol) in DMF (400 mL) was added sodium azide (23.2 g, 0.178 mol) and tetrabutylammonium iodide (0.526 g, 1.42 mmol), and then the reaction mixture was heated to 80° C. After 3 hours, the reaction mixture was cooled to ambient temperature, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was diluted with THF/water (250 mL/50 mL), and to this mixture was added triphenylphospine (36.7 g, 0.140 mol). After 2 hours, the reaction mixture was diluted with water and extracted with ethyl acetate (6×300 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on silica gel (3% methanol/DCM) to afford benzyl [(2R)-1-amino-3-methoxypropan-2-yl]carbamate. MS ESI calc'd. for C12H19N2O3 [M+H]+ 239. found 239. 1H NMR (400 MHz, CDCl3) δ 7.46-7.39 (m, 5H), 5.86 (d, J=7.2 Hz, 1H), 5.12-5.05 (m, 2H), 3.92 (bs, 1H), 3.55-3.49 (m, 2H), 3.34 (s, 3H), 2.93 (d, J=5.6 Hz, 2H), 1.91 (s, 2H).

Provenance & Evidence