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 404680ノート

反応式

HRID 404680 の反応式
[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

参加物

4

反応物 2

HCID 6259Phenacyl bromideHCID 86688939HCID 86688939、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

(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.

後処理

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

出典と根拠

ORDレコード
ord-9aab93d2271f477c9a6681b00c76579a
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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