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

HRID 404671노트

반응식

HRID 404671 반응식
[F:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=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].[F:1][C:2]1[CH:3]=[C:4]([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]([CH2:27][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:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 6259Phenacyl bromideHCID 86688932(R)-quinuclidin-3-yl 2-(3-fluorophenyl)-2-(piperidin-1-yl)acetate

생성물 1

HCID 86688933(3R)-3-(2-(3-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide수율 70.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

(R)-Quinuclidin-3-yl 2-(3-fluorophenyl)-2-(piperidin-1-yl)acetate (164 mg, 0.47 mmol) and 2-bromo-1-phenylethanone (104 mg, 0.52 mmol) were dissolved in acetonitrile (5 ml) and stirred at room temperature for 16 hours. The solvent was evaporated and the crude was triturated with Et2O, filtered under suction and washed with EtOAc and Et2O (1/1) to obtain (3R)-3-(2-(3-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (180.5 mg; 69.9% yield) as a white solid.

후처리

  1. customThe solvent was evaporated
  2. customthe crude was triturated with Et2O
  3. filtrationfiltered under suction
  4. washwashed with EtOAc and Et2O (1/1)

출처 및 근거

ORD 기록
ord-c00e6604ad494a0fbf685db8b986bb39
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748613B2

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