HCID 59135785, compound → Tetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

HRID 1972723Notes

Reaction equation

HRID 1972723 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]2[C:14](=[O:17])[O:15][CH2:16][CH:10]2[CH2:9]1)C1C=CC=CC=1>[Pd].CCO>[CH2:16]1[CH:10]2[CH2:9][NH:8][CH2:13][CH2:12][N:11]2[C:14](=[O:17])[O:15]1

Participants

4

Reactant 1

HCID 59135785HCID 59135785, compound

Product 1

HCID 22562207Tetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-oneYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

10% Palladium on carbon (18 mg, 20% by wt.) was placed under an inert atmosphere and suspended in EtOH (1 mL). A solution of 7-benzyl-hexahydro-oxazolo[3,4-a]pyrazin-3-one (90 mg, 0.39 mmol) dissolved in EtOH (3.8 mL) was added. The reaction mixture was placed under H2 atmosphere (1 atmosphere pressure) and stirred overnight. The resulting mixture was filtered through a pad of Celite® and the solvent was concentrated in vacuo to give 53.6 mg (97%) of the title compound as clear oil. 1H-NMR (300 MHz, CD3Cl) 4.36 (t, 1H), 3.89 to 3.81 (m, 1H), 3.79 to 3.69 (m, 2H), 3.10 to 2.88 (m, 3H), 2.67 to 2.50 (m, 2H), 2.00 to 1.90 (m, 1H).

Workup

  1. additionwas added
  2. filtrationThe resulting mixture was filtered through a pad of Celite®
  3. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-07d93527068e418dad8a76e54b7170a2
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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