Imidazole → HCID 71270630, compound

Participants

Reaction Steps

To a solution of rel-(1R,5R)-5-(hydroxymethyl)cyclopent-2-en-1-ol (47.20 g, 0.4135 mol), N,N-dimethylaminopyridine (2.52 g, 0.0207 mol) and 1H-imidazole (30.97 g, 0.4549 mol) in methylene chloride (800 mL, 10 mol) at 0° C. under an atmosphere of nitrogen was added tert-butyldimethylsilyl chloride (28.0 g, 0.186 mol). The reaction was stirred for at 0° C. for 2.5 h, at which time tert-butyldimethylsilyl chloride (28.0 g, 0.186 mol) was added. The reaction was stirred for 2 additional hours. The reaction was quenched by addition of saturated aqueous NaCl solution (200 mL) and water (200 mL). The layers were separated and the organic layer was washed with water (3×200 mL) and brine (1×200 mL), dried over Na2SO4, filtered and concentrated in vacuo. The material was used without further purification in the next step.

Provenance & Evidence