9-Nitro-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline hydrochloride → (+)-1,2,3,5,6,10b-Hexahydropyrrolo[2,1-a]isoquinolin-9-amine hydrochloride

Participants

Reaction Steps

A suspension (+)-9-nitro-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline hydrochloride (1.83 g, 7.18 mmol) and 10% Pd--C (0.2 g) in ethanol (150 ml) was hydrogenated at 50 psi for 0.75 h. The solution was filtered and the filtrate was concentrated to a volume of 25 ml. It was then heated to reflux to dissolve all of the solid and upon cooling the product precipitated. The title compound was isolated as a white solid (1.37 g, 85%), m.p. 239-41.5° C.; [α]D +62.5° (c 1.13, MeOH). This salt was a single enantiomer by chiral CE.

Provenance & Evidence