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

HRID 1315

反応式

HRID 1315 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-13330458b3c94465aa5dc67623f8b399
出典データセット
uspto-grants-1998_03
特許番号
US05723627

関連ノート

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