Ammonium formate → (7S,9AS)-7-(((tert-butyldimethylsilyl)oxy)methyl)octahydropyrazino[2,1-c][1,4]oxazine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (7S,9aS)-7-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-8-(phenylmethyl)octahydropyrazino[2,1-c][1,4]oxazine (D106, 22.2 g, 0.059 moles) in 660 ml of methanol at room temperature under nitrogen, palladium on carbon (10 wt %, wet, 6.28 g, 0.006 moles) and ammonium formate (37.2 g, 0.59 moles) were added. The resulting mixture was stirred at 80° C. for 1-1.5 hours. The resulting mixture was then allowed to cool down to room temperature and filtered over Celite. The filtrate was concentrated under vacuum to afford the title compound (16 g) as pale yellow oil.

Provenance & Evidence