Ethyl Acetate → 1,1-Dimethylethyl hexahydro-4-oxo-1,1-diphenylpyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

HRID 1713506Notes

Reaction equation

HRID 1713506 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH:6]1[C:18]([OH:31])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:4].[H-].[Na+].C(OCC)(=O)C>O1CCCC1>[O:4]=[C:3]1[CH2:2][O:31][C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]2[CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][N:5]12

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 684196211,1-Dimethylethyl 4-(chloroacetyl)-3-[hydroxy(diphenyl)methyl]piperazine-1-carboxylate

Product 1

HCID 231218541,1-Dimethylethyl hexahydro-4-oxo-1,1-diphenylpyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylateYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-(chloroacetyl)-3-[hydroxy(diphenyl)methyl]piperazine-1-carboxylate (0.28 g, 0.63 mmol) in tetrahydrofuran (5 mL) was added 60% sodium hydride (40 mg, 1.0 mmol), and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added ethyl acetate, and the resulting mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the title compound (0.24 g, yield 93%).

Workup

  1. washthe resulting mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b80e8206082545fab2d9f424dcad2d8e
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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