Diethyl Ether → tert-Butyl [(3S)-2-oxooxetan-3-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of dry PPh3 (72 h under vacuum in the presence of P2O5) (5 mmol) in dry CH3CN (31 mL), kept at −50° C. under N2, dimethylazodicarboxylate (5 mmol) and, after 20 min, a solution of 1 (4.47 mmol) in CH3CN (10.4 mL), were added dropwise. The mixture was stirred for 1.5 h at −50/−35° C. and concentrated. Purification of the residue by flash-chromatography (cyclohexane/EtOAc 8:2 to 6:4) gave crude 2, which was finally washed and triturated to afford a white solid. Mp 120-122° C. (Et2O). [α]D20=−27° (c 0.1, CH3CN). 1H NMR is in accordance with literature (Arnold, et al., 1985).

Provenance & Evidence