Imidazole → 3-(t-Butoxycarbonylamino)-2-hydroxypropyl Triisopropylsilyl Ether

Participants

Reaction Steps

To a 0° C. mixture of 3-(t-butoxycarbonylamino)-2-hydroxypropanol (22.5 g, 118 mmol), imidazole (8.8 g, 130 mmol) and DMF (450 ml) was added triisopropylsilyl chloride (25 mL, 118 mmol). The reaction was warmed to room temperature and stirred for 3 h. The reaction was concentrated to a slurry, CH2Cl2 was added, and the mixture filtered. The filtrate was washed with water (2×) and concentrated. The reaction was repeated. The combined crude product was chromatographed with SiO2 (hexanes to 30% EtOAc/hexanes) to give the title compound (62.2 g, 76%).

Provenance & Evidence