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Cesium carbonate → Methyl 3-(4-benzyloxycarbonylaminopiperidin-1-yl)benzoate

HRID 43824
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HRID 43824 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].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.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:64]1[CH2:69][CH2:68][CH:67]([NH:70][C:71](=[O:80])[O:72][CH2:73][C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)[CH2:66][CH2:65]1>O1CCOCC1.CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:73]([O:72][C:71]([NH:70][CH:67]1[CH2:68][CH2:69][N:64]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:65][CH2:66]1)=[O:80])[C:74]1[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 10796Cesium carbonateHCID 12070Methyl 3-bromobenzoateHCID 634876Binap, (A+-)-HCID 15143044-Cbz-aminopiperidine

생성물 1

HCID 68405998Methyl 3-(4-benzyloxycarbonylaminopiperidin-1-yl)benzoate수율 26.6%

시약·촉매·용매 4

HCID 167845
palladium(II) acetate
촉매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

Methyl 3-bromobenzoate (230 mg, 1.07 mmol), palladium acetate (12 mg, 0.054 mmol), BINAP (133 mg, 0.214 mmol) and cesium carbonate (767 mg, 2.35 mmol) were added to a solution of benzyl piperidin-4-yl-carbamate obtained in Example (192b) (248 mg, 0.817 mmol) in 1,4-dioxane (10 mL) and N,N-dimethylformamide (2.5 mL), and the mixture was stirred at 100° C. for 20 hours. The reaction solution was cooled, diluted with ethyl acetate, and washed with brine. The organic layer was dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/1) to obtain 80 mg of the title compound as a colorless oily substance (20%).

후처리

  1. temperatureThe reaction solution was cooled
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/1)

출처 및 근거

ORD 기록
ord-2d442424469f4ef68a66b1df757b2b4d
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08536197B2

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