4-Toluenesulfonyl chloride → HCID 86612725、化合物

HRID 2099533ノート

反応式

HRID 2099533 の反応式
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(Cl)Cl>[C:14]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:12][CH2:11][C@H:10]([O:13][S:33]([C:30]3[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=3)(=[O:35])=[O:34])[CH2:9]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chloride2 回HCID 8471Triethylamine2 回HCID 25242003HCID 25242003、化合物

生成物 1

HCID 86612725HCID 86612725、化合物収率 68.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(3S)-1-Diphenylmethyl-3-hydroxypyrrolidine (4.00 g) was dissolved in methylene chloride (11 mL), and the solution was stirred under cooling with ice. Triethylamine (3.3 mL) was added dropwise to the reaction mixture, and p-toluenesulfonyl chloride (3.61 g) was added to the resultant mixture, followed by stirring at room temperature for 12 hours and then at 40° C. for 4.5 hours. Since the starting materials partially remained unconsumed, triethylamine (1.1 mL) and p-toluenesulfonyl chloride (1.5 g) were added to the reaction mixture and then stirred for 24 hours. The reaction mixture was extracted with water and chloroform, and the organic layer was dried over sodium sulfate. The drying agent was removed through filtration, and the filtrate was concentrated under reduced pressure, to thereby yield crystalline residue. The residue was subjected to silica gel chromatography, to thereby give the target compound (4.40 g, yield 68.5%). The thus-obtained compound was purified through recrystallization from isopropyl alcohol.

後処理

  1. temperatureunder cooling with ice
  2. stirringby stirring at room temperature for 12 hours
  3. stirringstirred for 24 hours
  4. extractionThe reaction mixture was extracted with water and chloroform
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. customThe drying agent was removed through filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-cea132f5e26b4c44a7dc231aa9ecdefb
出典データセット
uspto-grants-2009_08
特許番号
US07569599B2

反応ノート

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