Ammonia → HCID 66956546, compound

Participants

Reaction Steps

A suspension of silyl ether 178 (7.35 g, 14.5 mmol) in a solution of 1% HCl in 95% EtOH (desilylation conditions described by Cunico et al., 1980) (150 mL) was stirred at room temperature for 4 h, and then kept at 4° C. for 12 h. The resulting solution was cooled (CO2/acetone), neutralised by dropwise addition of 7M NH3 in MeOH (9.8 mL) with stirring, and then concentrated to dryness and the residue was chromatographed on silica gel. Elution with 33-75% EtOAc/petroleum ether firstly gave foreruns, and then further elution with 75% EtOAc/petroleum ether and EtOAc gave 2-[(2-bromo-4-nitro-1H-imidazol-1-yl)methyl]-1,3-propanediol (179) (3.42, 85%) as a white solid: mp (MeOH/CH2Cl2/hexane) 110-112° C.; 1H NMR [(CD3)2SO] δ 8.50 (s, 1H), 4.65 (t, J=5.0 Hz, 2H), 4.07 (d, J=7.3 Hz, 2H), 3.41 (m, 4H), 2.06 (m, 1H). Anal. (C7H10BrN3O4) C, H, N.

Provenance & Evidence