Diethyl Ether → tert-butyl N-hydroxycarbamate

Participants

Reaction Conditions

Reaction Steps

To a -78° C. solution of 547 mg (3.44 mmol) of N-Boc glycinal (20) in 17 mL of diethyl ether was added 5.16 mL (10.3 mmol, 3 equiv) of isobutylmagnesium chloride (2.0M in diethyl ether). After five minutes, the solution was warmed to 0° C. and stirred for 24 h. The reaction mixture was then diluted with 300 mL of ethyl acetate, washed with 1N aqueous sodium bisulfate, dried over magnesium sulfate and concentrated. Purification by flash chromatography (20×150 mm silica gel, 30% ethyl acetate/hexane) gave 291 mg (39%) of the title compound as a clear oil: Rf 0.20 (30% ethyl acetate/hexane); 1H NMR (300 MHz, CDCl3) δ5.19 (br t, J=5.4 Hz, 1H), 3.69 (br m, 1H), 3.24-3.19 (br m, 1H), 3.09 (br s, 1H), 2.92 (br pent, J=6.4 Hz, 1H), 1.72 (hept, J=6.4 Hz, 1H), 1.45-1.29 (m, 1H), 1.39 (s, 9H), 1.15 (ddd, J=4.8, 8.7, 13.4 Hz, 1H), 0.86 (t, J=6.3 Hz, 6H); MS(FAB) 218 (M+1), 162.

Provenance & Evidence