Imidazole → (3R)-1-Benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidine

Participants

Reaction Steps

(3R)-1-Benzyl-3-hydroxypyrrolidine (500 μL) and imidazole (466 mg) were dissolved in N,N-dimethylformamide (15 mL), and tert-butyldiphenylsilyl chloride (1.57 mL) was added to the solution under ice cooling, followed by stirring at room temperature for 9 days. The solvent was distilled away under reduced pressure, and the residue was partitioned by adding methylene chloride and water. The organic layer was dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure. The residue was subjected to silica gel flash column chromatography (hexane ethyl acetate=3:1), to thereby give the title compound (1.27 g).

Provenance & Evidence