Phenacyl bromide → (3R)-3-(2-(4-chlorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 404680노트

반응식

HRID 404680 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:9]([O:11][C@@H:12]2[CH:17]3[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]3)[CH2:13]2)=[O:10])=[CH:4][CH:3]=1.[Br:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29]>C(#N)C>[Br-:26].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[C:9]([O:11][C@@H:12]2[CH:17]3[CH2:18][CH2:19][N+:14]([CH2:27][C:28](=[O:29])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)([CH2:15][CH2:16]3)[CH2:13]2)=[O:10])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 6259Phenacyl bromideHCID 86688939HCID 86688939, 화합물

생성물 1

HCID 86688940(3R)-3-(2-(4-chlorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide수율 63.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

(R)-quinuclidin-3-yl 2-(4-chlorophenyl)-2-(piperidin-1-yl)acetate (100 mg, 0.28 mmol) and 2-bromo-1-phenylethanone (60.3 mg, 0.30 mmol) were dissolved in acetonitrile (4 ml) and stirred at room temperature for 16 hours. The solvent was evaporated and the resulting residue was purified by flash chromatography (DCM/MeOH=9/1) to obtain (3R)-3-(2-(4-chlorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (98 mg, 63.3% yield) as white powder.

후처리

  1. customThe solvent was evaporated
  2. customthe resulting residue was purified by flash chromatography (DCM/MeOH=9/1)

출처 및 근거

ORD 기록
ord-9aab93d2271f477c9a6681b00c76579a
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748613B2

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