2-Chloroacetophenone → (S)-1-(2-oxo-2-phenyl-ethyl)-3-(2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane chloride

HRID 77036

反応式

HRID 77036 の反応式
[C:1]1([CH:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]([O:10][C@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29]>CCOC(C)=O>[Cl-:26].[O:29]=[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:27][N+:13]12[CH2:14][CH2:15][CH:16]([CH2:17][CH2:18]1)[C@H:11]([O:10][C:8](=[O:9])[CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12]2

参加物

4

反応物 2

HCID 107572-ChloroacetophenoneHCID 59401267(S)-quinuclidin-3-yl 2-phenyl-2-(phenylamino)acetate

生成物 1

HCID 86643222(S)-1-(2-oxo-2-phenyl-ethyl)-3-(2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane chloride収率 65%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (S)-quinuclidin-3-yl 2-phenyl-2-(phenylamino)acetate (50.0 mg, 0.15 mmol) in EtOAc (2 mL), is added 2-chloro-1-phenylethanone (23.0 mg, 0.15 mmol) and the reaction is stirred first at RT for 15 hours, then at 70° C. for 7 hours and finally at RT for 3 days. The solvent is removed and the resulting crude is triturated with i-Pr2O/Et2O (3/1) and then with i-Pr2O to achieve the title compound as a beige solid (47.7 mg, 65% yield, chloride salt, mixture of diastereoisomers).

後処理

  1. waitat 70° C. for 7 hours
  2. waitfinally at RT for 3 days
  3. customThe solvent is removed
  4. customthe resulting crude is triturated with i-Pr2O/Et2O (3/1)

出典と根拠

ORDレコード
ord-f0b1e68eb8f64ac8ba98295f9431b57e
出典データセット
uspto-grants-2014_09
特許番号
US08835682B2

関連ノート

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