1-Benzyl-4-[1-benzyloxy-3-(tert-butoxycarbonylamino)cyclobutan-3-yl]-2-pyrrolidone → 1-Benzyl-4-[3-(tert-butoxycarbonylamino)-1-hydroxycyclobutan-3-yl]-2-pyrrolidone

Participants

Reaction Steps

A 4.86 g (10.8 mmol) portion of 1-benzyl-4-[1-benzyloxy-3-(tert-butoxycarbonylamino)cyclobutan-3-yl]-2-pyrrolidone (Isomer B) was dissolved in 140 ml of ethanol, and the solution was mixed with 1 g of palladium hydroxide on carbon catalyst and subjected to 1 hour of catalytic reduction under a hydrogen pressure of 3 atmospheres and under irradiation of light. After removal of the catalyst by filtration, the solvent was evaporated and the resulting residue was purified by a silica gel column chromatography to give 4.01 g (quantitative) of the title compound. Thereafter, optical resolution of Isomers B1 and B2 as enantiomers originated from the pyrrolidine 4 position asymmetric carbon atom of the thus obtained compound was carried out by HPLC under the following conditions.

Provenance & Evidence