Tricyclohexylphosphine → tert-Butyl (4-cyclopropyl-2-methylphenyl)carbamate

HRID 1191673노트

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HRID 1191673 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([CH3:16])[CH:3]=1.O.[CH:18]1(B(O)O)[CH2:20][CH2:19]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH:18]1([C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([CH3:16])[CH:3]=2)[CH2:20][CH2:19]1

참가 물질

9

반응물 4

HCID 75806TricyclohexylphosphineHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 23074904N-Boc-4-iodo-2-methylanilineHCID 66762321Cyclopropylboronic acid monohydrate

생성물 1

HCID 86665748tert-Butyl (4-cyclopropyl-2-methylphenyl)carbamate수율 86.5%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A mixture of tert-butyl (4-iodo-2-methylphenyl)carbamate (1.04 g), cyclopropylboronic acid monohydrate (422 mg), palladium acetate (35.1 mg), tricyclohexylphosphine (87.5 mg), tripotassium phosphate monohydrate (2.52 g), toluene (8.7 mL) and water (0.87 mL) was stirred at 100° C. for 15 hours. The reaction mixture was allowed to cool to ambient temperature, diluted with ethyl acetate and filtered through celite (registered trademark). The filtrate was washed with water/saturated saline (1/1, 20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (668 mg).

후처리

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered through celite (registered trademark)
  3. washThe filtrate was washed with water/saturated saline (1/1, 20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-dc364dcc25f54f9bb832dc6c7c244abb
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680120B2

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