HCID 14076767, compound → (5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one

Participants

Reaction Steps

A solution of 9.25 g of the oily ethyl (4RS, 5S)-6-cyclohexyl-5-(t-butoxycarbonylamino)-4-hydroxy-2-hexynate (prepared as described in Preparation 4) in 100 ml of ethyl acetate was subjected to a catalytic hydrogenation reaction using a Paar's apparatus in the presence of 5 g of 5% w/w palladium-onbarium sulfate at about 4 atmospheres pressure for 4 hours. At the end of this time, the catalyst was removed by filtration, and the filtrate was condensed by evaporation under reduced pressure. The residue was then dissolved in 120 ml of toluene, 3 ml of acetic acid was added to the resulting solution, and the mixture was heated under reflux for 3 hours. The solvent was then removed by distillation under reduced pressure, and the residue was purified by medium pressure silica gel column chromatography (using a 2:1 by volume mixture of hexane and diethyl ether as eluent), to give 3.71 g [yield 35% from N-(t-butoxycarbonyl)-L-cyclohexylalaninol] of the title compound as the product of lesser polarity.

Provenance & Evidence