HCID 66589680, compound → HCID 66589844, compound

HRID 1911432Notes

Reaction equation

HRID 1911432 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[N:15]=[CH:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[N:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3]>C(O)C.[Pd]>[CH3:4][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]=[CH:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[N:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:1])[CH3:3]

Participants

4

Reactant 1

HCID 66589680HCID 66589680, compound

Product 1

HCID 66589844HCID 66589844, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium, 10% on carbon (21 mg, 0.20 mmol) and methyl 5-[1-[(2-methylpropan-2-yl)oxycarbonyl]-3,6-dihydro-2H-pyridin-4-yl]pyrazine-2-carboxylate (183 mg, 0.57 mmol) in ethanol (5.73 mL) was stirred under an atmosphere of hydrogen at ambient temperature and atmospheric pressure for 6 h. The reaction mixture was filtered through celite and concentrated under reduced pressure to give a yellow oil. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 50% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 5-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]pyrazine-2-carboxylate (126 mg, 68%) as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. customto give a yellow oil
  4. customThe crude product was purified by silica column chromatography
  5. washeluting with a gradient of 0 to 50% EtOAc in isohexane
  6. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-85a3ce13259043618d313d5a4c580a11
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

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