Benzoic Acid → HCID 56989727, compound

Participants

Reaction Steps

A solution of 0.52 ml (3.31 mmol) of diethyl azodicarboxylate in 5 ml of tetrahydrofuran was slowly added at room temperature to a solution of 1.00 g (3.25 mmol) of (2R, 3R)-1-t-butoxycarbonyl-2-benzyloxymethyl-3-hydroxypyrrolidine [prepared as described in step (a) above], 0.87 g (3.31 mmol) of triphenylphosphine and 0.42 g (3.47 mmol) of benzoic acid in 5 ml of tetrahydrofuran, and the mixture was stirred for 14 hours. At the end of this time, the reaction mixture was diluted with ethyl acetate and washed with a 5% w/v aqueous solution of citric acid, with a 5% w/v aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The reaction mixture was then dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by flash chromatography through silica gel, using a 20:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.05 g of the title compound as an oil.

Provenance & Evidence