4-Toluenesulfonyl chloride → 1-Benzyl-3-(p-toluenesulfonyl)aminomethylpyrrolidine

HRID 414216노트

반응식

HRID 414216 반응식
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH2:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][S:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=2)(=[O:23])=[O:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 3157467(1-Benzylpyrrolidin-3-yl)methanamine

생성물 1

HCID 139338051-Benzyl-3-(p-toluenesulfonyl)aminomethylpyrrolidine수율 58.7%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 1-benzyl-3-aminomethylpyrrolidine (J. Org. Chem. 26 4955, 1961; 5.0 g) in pyridine (30 ml) was added p-toluenesulfonyl chloride (5.6 g) for 5 minutes, and stirred for 2 hours at room temperature. After the reaction mixture was allowed to stand overnight and concentrated. The residue contain pyridine was removed by azeotrope with water (20 ml). A solution of the resulting residue in dichloromethane (100 ml) was washed with aqueous solution of potassium carbonate (x 2) and water, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography eluting with methanol:acetonitrile:dichloromethane (0:1:3→0.5:1:3) to give 1-benzyl-3-(p-toluenesulfonyl)aminomethylpyrrolidine (5.31 g) as liquid.

후처리

  1. waitto stand overnight
  2. concentrationconcentrated
  3. customwas removed by azeotrope with water (20 ml)
  4. washA solution of the resulting residue in dichloromethane (100 ml) was washed with aqueous solution of potassium carbonate (x 2) and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with methanol:acetonitrile:dichloromethane (0:1:3→0.5:1:3)

출처 및 근거

ORD 기록
ord-81617ba5605241b2a2a9e13ecc7698ab
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04791118

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