2-Chloroacetophenone → (R)-1-(2-oxo-2-phenylethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride

HRID 77035

反応式

HRID 77035 の反応式
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]1([C@@H:17]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:18]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]3)[CH2:22]2)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCOC(C)=O>[Cl-:1].[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][N+:23]12[CH2:24][CH2:25][CH:26]([CH2:27][CH2:28]1)[C@@H:21]([O:20][C:18](=[O:19])[C@@H:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:22]2

参加物

4

反応物 2

HCID 107572-ChloroacetophenoneHCID 46840261(R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate2 回

生成物 1

HCID 86691136(R)-1-(2-oxo-2-phenylethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride収率 56%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 2-chloroacetophenone (6.20 g, 40.3 mmol) and (R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate) (Diastereoisomer 1 of C2) (12.3 g, 36.6 mmol) in EtOAc (100 ml) is stirred at RT for 2 days (UPLC-MS monitoring: complete conversion). The solvent is evaporated and the crude is purified by flash chromatography eluting with DCM/MeOH=95/5 to get 10.1 g of the title compound as a white solid (56% yield, chloride salt, single diastereoisomer).

後処理

  1. customThe solvent is evaporated
  2. customthe crude is purified by flash chromatography
  3. washeluting with DCM/MeOH=95/5

出典と根拠

ORDレコード
ord-ddeddca527bb4283931aa5a8c21c58c8
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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