Triethylamine → HCID 67509425, compound

Participants

Reaction Conditions

Reaction Steps

To a cold, 0° C., solution of 3-amino-1-(benzyloxy)-3-methylbutan-2-ol (2 g, 9.6 mmol) and triethylamine (3.3 mL, 24 mmol) in 95 mL of anhydrous dichloromethane was added triphosgene (3.1 g, 10.5 mmol). The reaction was stirred at 0° C. for 3.5 hr and at RT for 1.5 hr. A solution of saturated sodium bicarbonate (95 mL) was added and the mixture was stirred for 15 min, then the organic layer was isolated and washed successively with 0.25N HCl, sat. NaHCO3, and brine. The organic layer was dried over sodium sulfate, concentrated to a residue and purified by column chromatography (30 to 75% ethyl acetate in hexanes) to give the title compound (1.8 g, 7.4 mmol, 78%). 1H NMR (CDCl3, 400 MHz) δ 1.27 (s, 3H), 1.40 (s, 2H), 1.90 3.67-3.76 (m, 2H), 4.37-4.41 (t, J=6.4 Hz, 1H), 4.56-4.64 (dd, J=9.6, 12 Hz, 2H), 5.27 (s, H), 7.28-7.40 (m, 5H). LRMS (ESI/APCI) m/z 236 [M+H]+.

Provenance & Evidence