Methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate → Methyl 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate

HRID 1808350Notes

Reaction equation

HRID 1808350 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]2[CH:14]=[N:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:10]2[CH2:9]1)C1C=CC=CC=1>CO>[C:16]1([C:17]([O:19][CH3:20])=[O:18])[N:15]=[CH:14][N:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]=12

Participants

3

Reactant 1

HCID 57635262Methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate

Product 1

HCID 68508140Methyl 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate (3.69 mmol) was dissolved in MeOH (20 ml), and the solution was flushed with nitrogen. Pd(OH)2 (250 mg) and a cat. amount of AcOH were added, and the mixture was again flushed with nitrogen for 20 min. The reaction mixture was reacted under a hydrogen atmosphere (50 psi) for 5 h on a Parr hydrogenation apparatus. Filtration over Celite was then carried out, followed by washing with methanol. The resulting crude product was purified by column chromatography (silica gel, 3-5% MeOH in DCM), and the desired product was thus obtained in the form of a yellow solid. Yield: 99%

Workup

  1. customthe solution was flushed with nitrogen
  2. additionamount of AcOH were added
  3. customthe mixture was again flushed with nitrogen for 20 min
  4. customThe reaction mixture was reacted under a hydrogen atmosphere (50 psi) for 5 h on a Parr hydrogenation apparatus
  5. filtrationFiltration over Celite
  6. washby washing with methanol
  7. customThe resulting crude product was purified by column chromatography (silica gel, 3-5% MeOH in DCM)

Sources & evidence

ORD record
ord-b3b1eafd5790499fa6d5dd526c1f1df9
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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