methyl oxo((phenylmethyl){[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}amino)acetate → (9aR)-8-(phenylmethyl)hexahydropyrazino[2,1-c][1,4]oxazine-6,7-dione

HRID 1366560Notes

Reaction equation

HRID 1366560 reaction equation
[O:1]=[C:2]([N:7]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:8][C@@H:9]1[CH2:14][O:13][CH2:12][CH2:11][N:10]1CC1C=CC=CC=1)[C:3](OC)=[O:4]>CO.[Pd]>[C:23]1([CH2:22][N:7]2[C:2](=[O:1])[C:3](=[O:4])[N:10]3[C@@H:9]([CH2:14][O:13][CH2:12][CH2:11]3)[CH2:8]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 1

HCID 66936387methyl oxo((phenylmethyl){[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}amino)acetate

Product 1

HCID 66936090(9aR)-8-(phenylmethyl)hexahydropyrazino[2,1-c][1,4]oxazine-6,7-dioneYield 86.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of crude methyl oxo((phenylmethyl){[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}amino)acetate (assumed 4.3583 g, 11.40 mmol) in MeOH (114 mL) was added 10% Pd/C (50% water, 870 mg). The mixture was hydrogenated under balloon pressure for 16 h, and then filtered through a 0.2 μm membrane. The solution was concentrated in vacuo, and the residue was triturated with 20% EtOAc-hexanes. The resulting solid was collected by vacuum filtration and washed with hexanes to provide (9aR)-8-(phenylmethyl)hexahydropyrazino[2,1-c][1,4]oxazine-6,7-dione (2.5610 g, 86% for 2 steps) as a light yellow solid. LCMS: (M+H)+: 261.1.

Workup

  1. filtrationfiltered through a 0.2 μm membrane
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was triturated with 20% EtOAc-hexanes
  4. filtrationThe resulting solid was collected by vacuum filtration
  5. washwashed with hexanes

Sources & evidence

ORD record
ord-7337c6eafa564870be718a43498a0686
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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