Stannous chloride dihydrate → 1-Benzyl-4-(3-chlorophenyl)pyrrolidin-3-amine

HRID 2066987노트

반응식

HRID 2066987 반응식
[CH2:1]([N:8]1[CH2:12][CH:11]([N+:13]([O-])=O)[CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH2:1]([N:8]1[CH2:9][CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[CH:11]([NH2:13])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 67218087(3SR,4RS)-1-Benzyl-3-(3-chloro-phenyl)-4-nitro-pyrrolidine

생성물 1

HCID 672180701-Benzyl-4-(3-chlorophenyl)pyrrolidin-3-amine수율 78.7%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of (3SR,4RS)-1-benzyl-3-(3-chloro-phenyl)-4-nitro-pyrrolidine (6.30 g, 19.8 mmol) in EtOAc (150 ml) was added portion wise SnCl2.2H2O (22.43 g, 99 mmol). The reaction mixture was then heated at reflux for 4 hours, cooled down to RT and a saturated aqueous solution of NaHCO3 (500 ml) was added. The salts were filtered off and the product extracted with EtOAc. The organic phases were then dried over Na2SO4, and concentration under vacuum. A column chromatography (CH2Cl2/MeOH 95/5) gave 4.47 g (78%) of the title compound as a light yellow oil. ES-MS m/e: 287.0 (M+H+).

후처리

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 4 hours
  3. filtrationThe salts were filtered off
  4. extractionthe product extracted with EtOAc
  5. dry with materialThe organic phases were then dried over Na2SO4, and concentration under vacuum

출처 및 근거

ORD 기록
ord-895a7d2918514a1ebe9f8a4eea8081d7
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293770B2

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