methyl (2R)-1-(N-{[(phenylmethyl)oxy]carbonyl}glycyl)-2-piperidinecarboxylate → (9aR)-octahydro-1H-pyrido(1,2-a)pyrazine-1,4-dione

HRID 1366594Notes

Reaction equation

HRID 1366594 reaction equation
C1(COC([NH:11][CH2:12][C:13]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]2[C:21]([O:23]C)=O)=[O:14])=O)C=CC=CC=1>CO>[C:21]1(=[O:23])[NH:11][CH2:12][C:13](=[O:14])[N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]12

Participants

3

Reactant 1

HCID 66936225methyl (2R)-1-(N-{[(phenylmethyl)oxy]carbonyl}glycyl)-2-piperidinecarboxylate

Product 1

HCID 66936119(9aR)-octahydro-1H-pyrido(1,2-a)pyrazine-1,4-dioneYield 76.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (2R)-1-(N-{[(phenylmethyl)oxy]carbonyl}glycyl)-2-piperidinecarboxylate (2.029 g, 6.068 mmol) was dissolved in MeOH (30 mL), degassed and placed under argon. 10% Pd/C (610 mg) was added, and the contents were thoroughly degassed and placed under a hydrogen balloon for 3 h. The contents were then degassed, and the Pd/C was removed by filtration through Celite, washing with MeOH. The filtrate was concentrated in vacuo to provide pure (9aR)-tetrahydro-2H-pyrido[1,2-a]pyrazine-1,4(3H,6H)-dione (779 mg, 76%). LCMS: (M+H)+: 169.1.

Workup

  1. customdegassed
  2. addition10% Pd/C (610 mg) was added
  3. customthe contents were thoroughly degassed
  4. customfor 3 h
  5. customThe contents were then degassed
  6. customthe Pd/C was removed by filtration through Celite
  7. washwashing with MeOH
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-448e1b1ef00645faab21406deed2153f
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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