Methyl N-{[(3R)-4-(phenylmethyl)-3-morpholinyl]carbonyl}-D-serinate → ((7S,9aS)-Octahydropyrazino[2,1-c][1,4]oxazin-7-yl)methanol

HRID 421192Notes

Reaction equation

HRID 421192 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[C:14]([NH:16][C@@H:17]([C:20](OC)=O)[CH2:18][OH:19])=O)C=CC=CC=1>CCO.CO.[Pd]>[CH2:10]1[C@@H:9]2[CH2:14][NH:16][C@H:17]([CH2:18][OH:19])[CH2:20][N:8]2[CH2:13][CH2:12][O:11]1

Participants

5

Reactant 1

HCID 59215767Methyl N-{[(3R)-4-(phenylmethyl)-3-morpholinyl]carbonyl}-D-serinate

Product 1

HCID 59215831((7S,9aS)-Octahydropyrazino[2,1-c][1,4]oxazin-7-yl)methanolYield 35%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Methyl N-{[(3R)-4-(phenylmethyl)-3-morpholinyl]carbonyl}-D-serinate (D48, 3.72 g, 11.55 mmol) was dissolved in EtOH (50 mL), treated with 10% Pd on C (450 mg) then placed under an atmosphere of hydrogen over the weekend. Left stirring for further 6 hours. Added 10% Pd on C (200 mg) and left under an atmosphere of hydrogen overnight. Catalyst removed by filtration through kieselguhr washed with acid, washing well with EtOH. Solvent removed under reduced pressure to afford a colourless oil. Oil dissolved in dry MeOH (15 mL) and heated at 50° C. overnight. Left heating for a further 3 hours before cooling to R.T. Solvent removed under reduced pressure. Residue triturated with DCM to afford the title compound as an off white solid in 35% yield over the 2 steps.

Workup

  1. waitLeft
  2. waitleft under an atmosphere of hydrogen overnight
  3. customCatalyst removed by filtration through kieselguhr
  4. washwashed with acid
  5. washwashing well with EtOH
  6. customSolvent removed under reduced pressure
  7. customto afford a colourless oil
  8. waitLeft
  9. temperatureheating for a further 3 hours
  10. temperaturebefore cooling to R.T
  11. customSolvent removed under reduced pressure
  12. customResidue triturated with DCM

Sources & evidence

ORD record
ord-0aee76bf66f745b093e47955588ee137
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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