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

HRID 414216ノート

反応式

HRID 414216 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 139338051-Benzyl-3-(p-toluenesulfonyl)aminomethylpyrrolidine収率 58.7%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-81617ba5605241b2a2a9e13ecc7698ab
出典データセット
uspto-grants-1988_12
特許番号
US04791118

反応ノート

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