Benzyl 5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-cyanophenoxy)-propyl]hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate → tert-Butyl (1S)-2-(4-cyanophenoxy)-1-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-ylmethyl)ethylcarbamate

Participants

Reaction Steps

Benzyl 5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-cyanophenoxy)-propyl]hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (3.6 g, 6.9 mmol; from step (i) above) was dissolved in ethanol (300 mL of 95%) and hydrogenated over 5% Pd/C (w/w). The reaction was stopped when the theoretical amount of H2 (173 mL) was consumed. The mixture was filtered (through Celite®) and then evaporated. Purification by chromatography on silica (DCM, 5% MeOH eluant) gave 1.7 g (63.6%) of the title compound.

Provenance & Evidence