Tetrahydrofuran → Tert-butyl 3-(3-(4-(methoxycarbonyl)phenoxy)pyrazin-2-yl)piperidine-1-carboxylate

HRID 555895Notes

Reaction equation

HRID 555895 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:30]=[CH:29][C:8]([O:9][C:10]2[C:11]([C:16]3[CH2:17][CH2:18][CH2:19][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:21]=3)=[N:12][CH:13]=[CH:14][N:15]=2)=[CH:7][CH:6]=1)=[O:4].C1COCC1>[Pd].CCO>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[C:11]([CH:16]3[CH2:17][CH2:18][CH2:19][N:20]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:21]3)=[N:12][CH:13]=[CH:14][N:15]=2)=[CH:29][CH:30]=1)=[O:4]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 59351326tert-butyl 5-(3-(4-(methoxycarbonyl)phenoxy)pyrazin-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 59351183Tert-butyl 3-(3-(4-(methoxycarbonyl)phenoxy)pyrazin-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a rb flask containing tert-butyl 5-(3-(4-(methoxycarbonyl)phenoxy)pyrazin-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate (900 mg, 2.187 mmol) and palladium on carbon (233 mg, 0.219 mmol) (10 wt %) under N2 is added THF (5.5 mL) and EtOH (5.5 mL). The flask is purged with H2 (3×), then stirred under H2 at rt 3 h. The reaction was filtered through celite and the filter cake washed with Teac (2×10 mL). The combined filtrates were concentrated and the residue purified by ISCO (12 g SiO2, 0-50% Teac/Hexane) to give tert-butyl 3-(3-(4-(methoxycarbonyl)phenoxy)pyrazin-2-yl)piperidine-1-carboxylate as a brown solid.

Workup

  1. customThe flask is purged with H2 (3×)
  2. filtrationThe reaction was filtered through celite
  3. washthe filter cake washed with Teac (2×10 mL)
  4. concentrationThe combined filtrates were concentrated
  5. customthe residue purified by ISCO (12 g SiO2, 0-50% Teac/Hexane)

Sources & evidence

ORD record
ord-4ad9163601214bfa9d4815096195a3a5
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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