Ammonia → 1-Benzoyl-trans-3-amino-4-methylthio-pyrrolidine

HRID 1315

반응식

HRID 1315 반응식
[C:1]([N:9]1[CH2:13][CH:12]=[CH:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][S:15](Cl)(=O)=O.[NH3:19].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.C(Cl)Cl>[C:1]([N:9]1[CH2:13][C@@H:12]([S:15][CH3:14])[C@H:11]([NH2:19])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 112522831H-Pyrrole, 1-benzoyl-2,5-dihydro-

생성물 1

HCID 702820171-Benzoyl-trans-3-amino-4-methylthio-pyrrolidine

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

41.5 g (0.24 mol) of 1-benzoyl-2,5-dihydropyrrole are initially introduced into 240 ml of methylene chloride, and 24.8 g (0.3 mol) of methanesulphonyl chloride are added dropwise at 0° C. The mixture is subsequently stirred at room temperature for 16 hours, the solvent is then stripped off under 8 mbar and the residue is taken up in 240 ml of tetrahydrofuran. After addition of 65 g of 25% strength ammonia solution, the mixture is heated at 80° C. in an autoclave for 10 hours. It is then poured into 5 times the amount of water, the pH is brought to 10-11 with sodium carbonate, the mixture is extracted with methylene chloride and the extract is dried over sodium sulphate and concentrated. The crude product (50 g) is chromatographed on silica gel (mobile phase initially ethanol:ethyl acetate 1:3, then ethanol; Rf value: 0.34 ethanol).

후처리

  1. additionare added dropwise at 0° C
  2. temperaturethe mixture is heated at 80° C. in an autoclave for 10 hours
  3. extractionthe mixture is extracted with methylene chloride
  4. dry with materialthe extract is dried over sodium sulphate
  5. concentrationconcentrated
  6. customThe crude product (50 g) is chromatographed on silica gel (mobile phase initially ethanol:ethyl acetate 1:3

출처 및 근거

ORD 기록
ord-13330458b3c94465aa5dc67623f8b399
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723627

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