Triethylamine → HCID 57295678, compound

Participants

Reaction Steps

To a solution of (2S,4R)-N-tert-butoxycarbonyl-2-(2-tert-butoxycarbonyl-1-oxoethyl)-4-tert-butyldimethylsiloxypyrrolidine (3.39 g, 7.64 mmol) in tetrahydrofuran (35 ml) was added a 1M tetrabutylammonium fluoride--tetrahydrofuran solution (8.41 ml, 8.41 mmol). This solution was stirred at room temperature for 8 h. Saturated aqueous ammonium chloride was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. The residue was dissolved in methylene chloride (50 ml), and triethylamine (3.22 ml, 22.9 mmol) and methanesulfonyl chloride (1.18 ml, 15.3 mmol) were successively dropwise added thereto at 0° C. The mixture was stirred at the same temperature for 2 h. Then, saturated aqueous ammonium chloride was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (heptane-ethyl acetate=1:1) to obtain the title compound (2.33 g, yield: 74.8%).

Provenance & Evidence