Ethyl Acetate → HCID 57273049, compound

Participants

Reaction Steps

Pyridinium dichromate was added to a solution of (2R, 4R)-N-tert-butoxycarbonyl-2-[(2S, 4R)-N-tert-butoxycarbonyl-2-(hydroxymethyl)pyrrolidin-4-ylmethyl]-4 -(tert-butyldimethylsiloxy)pyrrolidine (3.00 g, 5.84 mmol, compound of Reference Example 2-6) in N,N-dimethylformamide (30 ml) and stirred at room temperature for 14 hours. Ethyl acetate was added to the reaction solution and washed sequentially with water and a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel flash column chromatography (Wakogel™ C-300, 80 ml, n-hexane-ethyl acetate (1:1)) to obtain (2R, 4R)-N-tert-butoxycarbonyl-2-[(2S, 4R)-N-tert-butoxycarbonyl-2-carboxypyrrolidin-4-ylmethyl]-4-(tert-butyldimethylsiloxy)pyrrolidine (1.77 g, yield: 57%).

Provenance & Evidence