4-[2-(Pyrrolidin-1-yl)ethyl]piperidine → 2-((1-(4-Methoxy-2,6-dimethylphenylsulfonyl)pyrrolidin-2-yl)methoxy)-1-(4-(2-(pyrrolidin-1-yl)ethyl)piperidin-1-yl)ethanone

HRID 2090810ノート

反応式

HRID 2090810 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[CH2:17][CH2:16][CH2:15][CH:14]2[CH2:18][O:19][CH2:20][C:21]([OH:23])=O)(=[O:12])=[O:11])=[C:5]([CH3:24])[CH:4]=1.[N:25]1([CH2:30][CH2:31][CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH2:29][CH2:28][CH2:27][CH2:26]1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[CH2:17][CH2:16][CH2:15][CH:14]2[CH2:18][O:19][CH2:20][C:21]([N:35]2[CH2:34][CH2:33][CH:32]([CH2:31][CH2:30][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:37][CH2:36]2)=[O:23])(=[O:12])=[O:11])=[C:5]([CH3:24])[CH:4]=1

参加物

5

反応物 3

HCID 2962934-[2-(Pyrrolidin-1-yl)ethyl]piperidineHCID 516892Sodium BicarbonateHCID 59746454HCID 59746454、化合物

生成物 1

HCID 597464482-((1-(4-Methoxy-2,6-dimethylphenylsulfonyl)pyrrolidin-2-yl)methoxy)-1-(4-(2-(pyrrolidin-1-yl)ethyl)piperidin-1-yl)ethanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

N,N′-Carbonyldiimidazole (71 mg, 0.441 mmol) was added to a solution of 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)pyrrolidin-2-yl)methoxy)acetic acid (150 mg, 0.420 mmol) in dichloromethane (7 ml), and the mixture was stirred for 1 h at room temperature. A solution of 4-(2-(pyrrolidin-1-yl)ethyl)piperidine (76 mg, 0.420 mmol) in dichloromethane (3 ml) was then added, and the reaction mixture was stirred for 15 h at room temperature. Saturated sodium hydrogen carbonate solution (10 ml) was then added to the reaction mixture, and then the aqueous phase was extracted with dichloromethane (2×10 ml). The combined organic phases were extracted with saturated sodium chloride solution (10 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography using ethyl acetate/methanol/ammonia solution (25% aq.) (400:100:5).

後処理

  1. stirringthe reaction mixture was stirred for 15 h at room temperature
  2. extractionthe aqueous phase was extracted with dichloromethane (2×10 ml)
  3. extractionThe combined organic phases were extracted with saturated sodium chloride solution (10 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-b10f6f0963d64ef4833f97aa3712a494
出典データセット
uspto-grants-2013_05
特許番号
US08435978B2

反応ノート

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