HCID 14500594, compound → HCID 14500599, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3 g (90 mmol) of 1-butyl-2-(3'-ureidobenzyl)-5-propylpyrrole in 150 ml of glacial acetic acid was hydrogenated at 45 p.s.i. in the presence of 2 g of 5% rodium on activated alumina as catalyst, for 41/2 hours. The catalyst was then separated by filtration and the filtrate evaporated in vacuo. The residue was suspended in 100 ml of ethyl acetate, cooled to 0° C. and 30 ml of concentrated ammonium hydroxide was added thereto. The organic phase was separated, dried and evaporated in vacuo. The residue was purified by t.l.c. using a (50:50) mixture of chloroform-[chloroform:methanol:ammonium hydroxide (60:10:1)] as the eluant, to produce 1.1 g (37%) of the less polar cis-1-butyl-2-(3'-ureidobenzyl)-5-propylpyrrolidine isomer, and 150 mg (5%) of the more polar trans-1-butyl-2-(3'-ureidobenzyl)-5-propylpyrrolidine isomer, which was recrystallized from ether hexane.

Provenance & Evidence