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

HRID 2245449Notes

Reaction equation

[CH3:1][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][C@@H:8]1[CH2:17][N:16]2[C@H:11]([CH2:12][O:13][CH2:14][CH2:15]2)[CH2:10][N:9]1CC1C=CC=CC=1)([CH3:4])[CH3:3].C([O-])=O.[NH4+]>CO.[Pd]>[CH3:4][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][C@@H:8]1[CH2:17][N:16]2[C@H:11]([CH2:12][O:13][CH2:14][CH2:15]2)[CH2:10][NH:9]1)([CH3:1])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

temperatureto cool down to room temperature
filtrationfiltered over Celite
concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record: ord-63a2c91276d9460ba93b686176dcb8f7
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683056B2

Reaction notes

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