Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylate → (4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-(tert-butoxycarbonylamino)thiazole-4-carboxylate 88 (10.5 g, 38.6 mmol) was dissolved in 300 mL of anhydrous THF and cooled in dry ice-acetonitrile bath. A solution of 1 M Super Hydride™ in THF (85 mL) was then added over a period of 10 min. The resulting reaction mixture was stirred at −45° C. for 2 h. Another portion of 1 M Super Hydride™ in THF (35 mL) was then added and the reaction mixture was stirred for an additional 2 h at −45° C. The reaction was quenched at −45° C. by the addition of 50 mL of brine. Upon warming to room temperature, the reaction mixture was concentrated under reduced pressure. The resulting mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by chromatography to afford 89 (6.39 g, 72% yield).

Provenance & Evidence