Binap, (A+-)- → HCID 66799007, compound

HRID 1193398

Reaction equation

HRID 1193398 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Cl[C:17]1[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][N:2]([CH:10]1[CH2:11][CH2:12][N:13]([C:17]2[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=2)[CH2:14][CH2:15]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 3

HCID 634876Binap, (A+-)-HCID 27568064-N-Boc-4-N-Methyl-aminopiperidineHCID 71700952-Chloro-6-methylpyrazine

Product 1

HCID 66799007HCID 66799007, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

KOBut (483 mg, 4.32 mmol, 2.5 eq) was added at room temperature to a solution of tert-butyl methyl(piperidin-4-yl)carbamate (stage 3 AMN-60) (370 mg, 1.72 mmol, 1 eq) and 2-chloro-6-methylpyrazine (244 mg, 1.9 mmol, 1.1 eq) in toluene (50 ml) and the mixture was degassed for 30 min with argon. BINAP (64.5 mg, 0.103 mmol, 0.06 eq) and Pd2(dba)3 (31.6 mg, 0.034 mmol, 0.02 eq) were added and the reaction mixture was refluxed for 16 h. After cooling, concentration under reduced pressure was carried out. The residue was taken up in dichloromethane (50 ml) and washed with water (30 ml) and saturated sodium chloride solution (30 ml) and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure and the crude product so obtained was purified by column chromatography (Alox, 0.5% methanol/dichloromethane). The desired product was in the form of a brown solid. Yield: 47% (250 mg, 0.816 mmol)

Workup

  1. customthe mixture was degassed for 30 min with argon
  2. temperaturethe reaction mixture was refluxed for 16 h
  3. temperatureAfter cooling
  4. concentrationconcentration under reduced pressure
  5. washwashed with water (30 ml) and saturated sodium chloride solution (30 ml)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-a1044dc86d6d4014993a32f2ef429826
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Linked notes

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