Imidazole → tert-butyl N-[(1R)-1-[4-(iodomethyl)-1,3-oxazol-2-yl]ethyl]carbamate

Participants

Reaction Steps

To a solution of TPP (873 mg, 3.33 mmol) in CH2Cl2 (10 mL), was added I2 (845 mg, 3.33 mmol), and stirred for 10 min. Imidazole (227 mg, 3.33 mmol) was added and stirred for an additional 10 min and then a solution of (R)-tert-butyl 1-(4-(hydroxymethyl)oxazol-2-yl)ethylcarbamate (537 mg, 2.22 mmol) in CH2Cl2 (15 mL) was added. After 2 h, the reaction mixture was washed successively with sat. aq. NaHCO3, aq. Na2S2O3, dried on Na2SO4 and concentrated under low pressure. The residue was chromatographed on silica gel (20% ethyl acetate/80% hexanes) to yield 84% of (R)-tert-butyl 1-(4-(iodomethyl)oxazol-2-yl)ethylcarbamate.

Provenance & Evidence