Ethyl Acetate → Tert-butyl 1'-(5-methylpyrazin-2-yl)-4,4'-bipiperidine-1-carboxylate

HRID 2093464Notes

Reaction equation

HRID 2093464 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[N:24][C:23](Cl)=[CH:22][N:21]=3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][Mg]Br.[Cl-].N.C(OCC)(=O)C>C1COCC1.CN1C(=O)CCC1.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Fe]>[CH3:27][C:23]1[N:24]=[CH:25][C:20]([N:17]2[CH2:18][CH2:19][CH:14]([CH:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]3)[CH2:15][CH2:16]2)=[N:21][CH:22]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 20976574Ammonia chlorideHCID 59178890Tert-butyl 1'-(5-chloropyrazin-2-yl)-4,4'-bipiperidine-1-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 59178865Tert-butyl 1'-(5-methylpyrazin-2-yl)-4,4'-bipiperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 11110968Iron (III) acetylacetonateCatalystHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The tert-butyl-1′-(5-chloropyrazin-2-yl)-4,4′-bipiperidine-1-carboxylate (1.1 g, 2.9 mmol) was dissolved in 1:1 THF and NMP (30 mL) at r.t. Iron (III) acetylacetonate (512 mg, 1.45 mmol) was added under N2. Methyl magnesium bromide (3M, 3.9 mL, 11.6 mmol) was added dropwise and the mixture stirred for 15 min. An ice cooled solution of saturated ammonia chloride (30 mL, aq.) and ethyl acetate (30 mL) were added, the mixture shaken, and the phases separated. The organic phase was washed with brine (10 mL, ×1), dried over magnesium sulfate, filtered, and concentrated in vac. The residue was purified by chromatography on silica gel with 12.5% acetone: hexanes to yield the title compound.

Workup

  1. stirringthe mixture shaken
  2. customthe phases separated
  3. washThe organic phase was washed with brine (10 mL, ×1)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vac
  7. customThe residue was purified by chromatography on silica gel with 12.5% acetone

Sources & evidence

ORD record
ord-7d73504b32544c3da6032f97882c0d54
Source dataset
uspto-grants-2013_05
Patent number
US08445499B2

Reaction notes

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