(Trimethylsilyl)imidazole → HCID 72485669, compound

Participants

Reaction Steps

A solution of rac-(4R,5S,6S)-1-benzyloxy-6-tert-butyldimethylsilyloxy-5-hydroxy-1-azaspiro[3.5]nona-8-ene-2,7-dione (3) (130 mg, 0.322 mmol) in 1-trimethylsilylimidazole (0.5 ml, 3.220 mmol) was stirred at room temperature for 16 h. The reaction was quenched with Na2PO4 0.1 M buffer (2 ml) and the mixture extracted with AcOEt (3×4 ml). The combined extracts were washed with saturated aqueous CuSO4 solution (1×8 ml) and brine (2×8 ml), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-AcOEt, 5:1) to give rac-(4R,5S,6S)-1-benzyloxy-6-tert-butyldimethylsilyloxy-5-trimethylsilyloxy-1-azaspiro[3.5]nona-8-ene-2,7-dione (6) as a white solid (100 mg, 65%).

Provenance & Evidence