Triphenylphosphine → HCID 131722212, compound

Participants

Reaction Steps

49.9 g (98.1 mmole) of 4-t-butyldimethylsilyloxy-(2R)-(3,4-dichlorophenyl)-1-[N-(t-butoxycarbonyl)-N-(2-hydroxyethyl)amino]-2-butanol [prepared as described in step (a) above] and 30.9 g (118 mmole) of triphenylphosphine were dissolved in 600 ml of dried toluene. 51.3 g of a 40% w/v toluene solution containing 118 mmole of diethyl azodicarboxylate were added dropwise to the resulting solution at room temperature under a nitrogen atmosphere, and the mixture was stirred for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of hexane and ethyl acetate ranging from 47:3 to 23:2 by volume as the eluent, to give 43.2 g of the title compound.

Provenance & Evidence