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 404671ノート

反応式

HRID 404671 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

(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.

後処理

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

出典と根拠

ORDレコード
ord-c00e6604ad494a0fbf685db8b986bb39
出典データセット
uspto-grants-2014_06
特許番号
US08748613B2

反応ノート

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