Binap, (A+-)- → HCID 66799007, 화합물

HRID 1193398노트

반응식

HRID 1193398 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 66799007HCID 66799007, 화합물수율 47%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-a1044dc86d6d4014993a32f2ef429826
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680159B2

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