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

반응식

HRID 2090810 반응식
[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

참가 물질

5

반응물 3

HCID 2962934-[2-(Pyrrolidin-1-yl)ethyl]piperidineHCID 516892Sodium BicarbonateHCID 59746454HCID 59746454, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b10f6f0963d64ef4833f97aa3712a494
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08435978B2

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