Sodium borohydride → tert-Butyl (4-(2-hydroxyethyl)thiazol-2-yl)carbamate

Participants

Reaction Steps

To a solution of (2-tert-Butoxycarbonylamino-thiazol-4-yl)-acetic acid ethyl ester (4 g, 13.9 mmol) in EtOH (50 ml), NaBH4 (1.59 g, 41.9 mmol) was added at 0° C. and stirred at r.t. for 18 h. Solvent was removed under reduced pressure and extracted in Ethyl acetate (150 ml) washed with brine (2×30 ml) dried over Na2SO4. After evaporation, the residue was purified by preparative chromatography (1:3 EtOAc:Hexanes) to give [4-(2-Hydroxy-ethyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (2.2 g, 65%). 1H NMR (400 MHz, CDCl3): 1.): 1.53 (s, 9H), 2.87 (t, J=5.2 2H), 3.90 (t, J=5.2 Hz, 2H), 6.55 (s, 1H). MS (EI) m/z: 245 (M+1).

Provenance & Evidence