HCID 66936464, compound → HCID 66936137, compound

HRID 1366665Notes

Reaction equation

HRID 1366665 reaction equation
[CH3:1][N:2]1[C@H:11]2[C@H:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[N:5](C(OCC2C=CC=CC=2)=O)[CH2:4][CH2:3]1>CO>[CH3:1][N:2]1[C@H:11]2[C@H:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[NH:5][CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 66936464HCID 66936464, compound

Product 1

HCID 66936137HCID 66936137, compoundYield 144.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phenylmethyl (4aR,8aS)-4-methyloctahydro-1(2H)-quinoxalinecarboxylate (Example 221) (2.58 g, 9.0 mmol) was dissolved in 120 mL of MeOH, degassed and placed under argon. 10% Pd/C (380 mg) was added, and the contents were thoroughly degassed and placed under a hydrogen balloon for approximately 2 hrs. The contents were then degassed and filtered through Celite, and the Celite pad was washed with DCM and MeOH. After 19.0 mL 1N HCl was added, the resulting filtrate was concentrated in vacuo to provide the hydrochloride salt of (4aS,8aR)-1-methyldecahydroquinoxaline (2.0 g, 100%). LCMS: (M+H)+: 155.1.

Workup

  1. customdegassed
  2. addition10% Pd/C (380 mg) was added
  3. customthe contents were thoroughly degassed
  4. customfor approximately 2 hrs
  5. customThe contents were then degassed
  6. filtrationfiltered through Celite
  7. washthe Celite pad was washed with DCM and MeOH
  8. additionAfter 19.0 mL 1N HCl was added
  9. concentrationthe resulting filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d0e59e42d10f4c269c3f6716f50ab3b2
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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