Isopropanol → Pyrazino[2,1-c][1,4]oxazine, octahydro-, (9aR)- (9CI)

HRID 2066532Notes

Reaction equation

HRID 2066532 reaction equation
[CH2:1]1[C@H:6]2[CH2:7][NH:8][CH2:9][CH2:10][N:5]2[C:4](=O)[CH2:3][O:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CC(O)C.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1>[CH2:1]1[C@H:6]2[CH2:7][NH:8][CH2:9][CH2:10][N:5]2[CH2:4][CH2:3][O:2]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 24436Sodium Sulfate2×HCID 16124470(9aR)-Hexahydropyrazino[2,1-c][1,4]oxazin-4(3H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 18649033Pyrazino[2,1-c][1,4]oxazine, octahydro-, (9aR)- (9CI)Yield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-hexahydro-pyrazino[2,1-c][1,4]oxazin-4-one (60 mg, 0.39 mmol) in dioxane (5 mL) was added LiAlH4 (1.5 mL, 1M solution in THF). The resulting mixture was heated at 80° C. for 2.5 h before the addition of iPrOH (0.5 mL) followed by a saturated aqueous solution of Na2SO4 (3 mL). Further Na2SO4 was added and the resulting mixture filtered through celite, washing with EtOAc. The resulting residue was purified by NH2 column to give the title compound as an oil (40 mg, 73%).

Workup

  1. filtrationthe resulting mixture filtered through celite
  2. washwashing with EtOAc
  3. customThe resulting residue was purified by NH2 column

Sources & evidence

ORD record
ord-0de7cf8cbd134b419f5ede457cf48a8c
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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