Acetonitrile → 3-(((4-Methoxyphenyl)(phenyl)methoxy)carbonyl)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 1910509노트

반응식

HRID 1910509 반응식
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH2:2]2.[Cl:27][CH2:28][C:29]([C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)=[O:30].C(#N)C>CCOC(C)=O>[Cl-:27].[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:11][C:9]([CH:3]2[CH:4]3[CH2:5][CH2:6][N+:1]([CH2:28][C:29](=[O:30])[C:31]4[S:32][CH:33]=[CH:34][CH:35]=4)([CH2:8][CH2:7]3)[CH2:2]2)=[O:10])=[CH:20][CH:21]=1

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 27579252-(Chloroacetyl)thiopheneHCID 70925768(4-Methoxyphenyl)(phenyl)methyl quinuclidine-3-carboxylate

생성물 1

HCID 706737583-(((4-Methoxyphenyl)(phenyl)methoxy)carbonyl)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride수율 31.2%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (4-methoxyphenyl)(phenyl)methyl quinuclidine-3-carboxylate (37 mg, 0.10 mmol) in EtOAc (1.5 ml), 2-chloro-1-(thiophen-2-yl)ethanone (19 mg, 0.12 mmol) was added. Acetonitrile was added until complete dissolution, and the reaction was stirred at room temperature overnight. The organic solvents were removed under vacuum, and the residue was purified by flash chromatography (DCM/MeOH=9/1) to obtain 3-(((4-methoxyphenyl)(phenyl)methoxy)carbonyl)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (16 mg, mixture of diastereoisomers).

후처리

  1. customThe organic solvents were removed under vacuum
  2. customthe residue was purified by flash chromatography (DCM/MeOH=9/1)

출처 및 근거

ORD 기록
ord-ec50e39e0d854d449ab0d0f9d774be58
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604015B2

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