Cesium carbonate → 1-(3-Phenylsulfonylphenyl)-4-tert-butyloxycarbonylpiperazine

HRID 855513노트

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HRID 855513 반응식
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:53]1([S:59]([C:62]2[CH:63]=[C:64](Br)[CH:65]=[CH:66][CH:67]=2)(=[O:61])=[O:60])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.[C:69]([O:73][C:74]([N:76]1[CH2:81][CH2:80][NH:79][CH2:78][CH2:77]1)=[O:75])([CH3:72])([CH3:71])[CH3:70]>O1CCOCC1>[C:53]1([S:59]([C:62]2[CH:63]=[C:64]([N:79]3[CH2:78][CH2:77][N:76]([C:74]([O:73][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:75])[CH2:81][CH2:80]3)[CH:65]=[CH:66][CH:67]=2)(=[O:61])=[O:60])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 640920Benzene, 1-bromo-3-(phenylsulfonyl)-

생성물 1

HCID 688047411-(3-Phenylsulfonylphenyl)-4-tert-butyloxycarbonylpiperazine수율 71.2%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A solution of 2 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (62 mg, 0.1 mmol) and cesium carbonate (329 mg, 1.01 mmol) in dry dioxane (2 ml) were sonicated for 45 min, under argon. To this solution was added 3-phenylsulfonylbromobenzene (D2) (200 mg, 0.67 mmol) and 1-(tert-butyloxycarbonyl)piperazine (314 mg, 1.68 mmol) and the reaction heated at 100° C. for 18 h. The reaction mixture was evaporated in vacuo and the residue partitioned between water (50 ml) and dichloromethane (50 ml). The organic layer was washed with sat. sodium hydrogen carbonate (50 ml), 10% citric acid (50 ml), brine (50 ml) and then dried (MgSO4). Solvents evaporated in vacuo and the residue purified by column chromatography (silica gel; 0-60% ethyl acetate/petroleum ether) to give the product as a colourless oil (192 mg, 71%)

후처리

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue partitioned between water (50 ml) and dichloromethane (50 ml)
  3. washThe organic layer was washed with sat. sodium hydrogen carbonate (50 ml), 10% citric acid (50 ml), brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. customSolvents evaporated in vacuo
  6. customthe residue purified by column chromatography (silica gel; 0-60% ethyl acetate/petroleum ether)

출처 및 근거

ORD 기록
ord-ddeb902ce7a64ae688d3c01c150e46fa
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262188B2

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