Sodium hydride → 1,1-dimethylethyl 1,1-bis(phenylmethyl)-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate

HRID 1713541Notes

Reaction equation

HRID 1713541 reaction equation
CC([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[C:21](O)([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:7])(C)C.[H-].[Na+]>CN(C)C=O>[C:23]1([CH2:22][C:21]2([CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:9]3[CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13][N:8]3[C:6](=[O:5])[O:7]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69645682Bis(1,1-dimethylethyl)2-[1-hydroxy-2-phenyl-1-(phenylmethyl)ethyl]-1,4-piperazinedicarboxylate

Product 1

HCID 231218621,1-dimethylethyl 1,1-bis(phenylmethyl)-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylateYield 82.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bis(1,1-dimethylethyl)2-[1-hydroxy-2-phenyl-1-(phenylmethyl)ethyl]-1,4-piperazinedicarboxylate (2.0 g, 4.0 mmol) was dissolved in N,N-dimethylformamide (20 mL). 60% Sodium hydride (0.19 g, 4.8 mmol) was added thereto, and the mixture was stirred at room temperature for 6 hours. The resulting mixture was extracted with ethyl acetate, washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue was added diisopropyl ether, and the obtained crystals were collected by filtration and washed with diisopropyl ether to obtain the title compound (1.4 g, yield 82%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washwashed with a 0.5 M aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added diisopropyl ether
  6. filtrationthe obtained crystals were collected by filtration
  7. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-6da43fdf5b5441b1b08946bb0425d800
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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