Water → 1-Benzhydrylazetidin-3-yl 4-methylbenzenesulfonate

HRID 1457994노트

반응식

HRID 1457994 반응식
[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C1C=CC=CN=1)C.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1.O>N1C=CC=CC=1>[CH:1]([N:14]1[CH2:17][CH:16]([O:18][S:34]([C:31]2[CH:32]=[CH:33][C:28]([CH3:38])=[CH:29][CH:30]=2)(=[O:36])=[O:35])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 218852-DimethylaminopyridineHCID 3304481-(Diphenylmethyl)azetidin-3-ol

생성물 1

HCID 155126511-Benzhydrylazetidin-3-yl 4-methylbenzenesulfonate수율 73.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To 2.39 g (10 mmol) of 1-benzhydryl-3-hydroxyazetidine dissolved in 20 ml of pyridine were added 1.46 g (12 mmol) of dimethylaminopyridine. Thereto was added 12.10 g (11 mmol) of p-toluenesulfonyl chloride at -40° C., followed by gradual increase in the temperature and subsequent 1 day of stirring at room temperature. This was mixed with 150 ml of water, extracted with chloroform (100 ml×3) and then dried over anhydrous sodium sulfate. After evaporation of the solvent, the resulting residue was purified by a silica gel column chromatography (250 ml, ethyl acetate:hexane 1:2) to yield 2.88 g (73%) of the title compound.

후처리

  1. temperatureby gradual increase in the temperature and subsequent 1 day
  2. extractionextracted with chloroform (100 ml×3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter evaporation of the solvent
  5. customthe resulting residue was purified by a silica gel column chromatography (250 ml, ethyl acetate:hexane 1:2)

출처 및 근거

ORD 기록
ord-6f5f54ba5f9b4d559c17be52ce933a51
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849757

반응 노트

불러오는 중…