Riboflavin → Tert-butyl 4-(3-(4-aminophenoxy)pyrazin-2-yl)piperidine-1-carboxylate

Participants

Reaction Steps

A solution of tert-butyl 4-(3-(4-aminophenoxy)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.87 g, 7.79 mmol) in 1,4-dioxane (39 mL) was added palladium hydroxide, 20 wt. % Pd (dry basis) on carbon, wet, Degussa type E101 NEW (0.27 g, 0.39 mmol) and hydrogenated (double-walled balloon pressure) at room temperature for 1 day. The reaction was filtered via a pad of Celite, and the filtrate was concentrated in vacuo and chromatographed via flash column chromatography (20% to 60% EtOAc/Hexanes) to provide tert-butyl 4-(3-(4-aminophenoxy)pyrazin-2-yl)piperidine-1-carboxylate as a cream solid. MS (ESI, pos. ion) m/z: 393.0 [M+1+Na].

Provenance & Evidence