HCID 15123261, compound → HCID 131717375, compound

Participants

Reaction Steps

A solution of the product of stage (i) (4.1 g) in glacial acetic acid (80 ml) was hydrogenated at 22° and atmospheric pressure over Adams' catalyst (3 g). After 3 h the uptake of hydrogen was complete and the mixture was filtered. The filtrate was evaporated to leave an oil which was partitioned between 2N sodium carbonate solution (100 ml) and dichloromethane (100 ml). The aqueous phase was further extracted with dichloromethane (100 ml). The combined organic extracts were washed with saturated brine, dried and evaporated to leave an oil (5.0 g). The oil was purified by flash chromatography eluting with a mixture of dichloromethane, ethanol and ammonia (200:8:1) to give the title compound as an oil (2.6 g). N.m.r.-indicates mixture of cis:trans (3:1). T.l.c. Silica (Dichloromethane:ethanol: 0.88 ammonia 100:8:1) Rf 0.4.

Provenance & Evidence