Diethyl Ether → (3R)-3-(2-(4-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 404685노트

반응식

HRID 404685 반응식
[Cl:1][CH2:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[C:18]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]3)[CH2:22]2)=[O:19])=[CH:13][CH:12]=1.CCOCC>CCOC(C)=O>[Cl-:1].[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([N:29]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]2)[C:18]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N+:23]([CH2:2][C:3](=[O:4])[C:5]4[S:6][CH:7]=[CH:8][CH:9]=4)([CH2:24][CH2:25]3)[CH2:22]2)=[O:19])=[CH:13][CH:12]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 27579252-(Chloroacetyl)thiopheneHCID 86688942(R)-quinuclidin-3-yl 2-(4-fluorophenyl)-2-(piperidin-1-yl)acetate

생성물 1

HCID 86688945(3R)-3-(2-(4-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride수율 26.7%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

2-Chloro-1-(thiophen-2-yl)ethanone (30.6 mg, 0.19 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(4-fluorophenyl)-2-(piperidin-1-yl)acetate (60 mg, 0.17 mmol) in EtOAc (3 ml). The reaction was stirred at room temperature for 16 hours. Et2O was added the precipitate was collected by filtration and purified by flash chromatography (DCM/MeOH/NH4OH=97/3/0.3) to obtain (3R)-3-(2-(4-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (23 mg, 26.2% yield) as a white solid.

후처리

  1. filtrationwas collected by filtration
  2. custompurified by flash chromatography (DCM/MeOH/NH4OH=97/3/0.3)

출처 및 근거

ORD 기록
ord-6318319131db4fd8a7736c6a7ee31437
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748613B2

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