Methanol → HCID 86634393, compound

Participants

Reaction Steps

2.0 M of a solution of (trimethylsilyl)diazomethane in hexane (40 mL) was added dropwise to 1-tert-butyl 2-methyl (2S,3S)-3-{[tert-butyl(diphenyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate (11.6 g) and methanol (50 mL) with stirring. The reaction solution was concentrated and the residue was added dimethylformamide (100 mL), tert-butyldiphenylchlorosilane (13.7 mL) and imidazole (6.37 g) and stirred at room temperature for overnight. The reaction solution was added water and extracted with a mixture solution of hexane/ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was added tetrahydrofuran (100 mL), methanol (3 mL) and lithium borohydride (2.51 g) at 0° C. and stirred at room temperature for 1 hour. The reaction solution was added water and aqueous 5% potassium sulfate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→75:25) to obtain the title compound (22.7 g) having the following physical properties.

Provenance & Evidence