Sodium Thiosulfate → Ethyl 1-(3-(2-thienyl)propionyl)-3-piperidinecarboxylate

HRID 432808ノート

反応式

HRID 432808 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11]1)=[O:9].O.NN.I([O-])(=O)(=O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CS(C)=O.S([O-])([O-])(=O)=O.[Cu+2].C(O)(=O)C.O.ClCCl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11]1)=[O:9]

参加物

10

反応物 4

HCID 24477Sodium ThiosulfateHCID 24654Hydrazine hydrate (1:1)HCID 23667635Sodium periodateHCID 54520739Ethyl 1-(3-(2-thienyl)acrylyl)-3-piperidinecarboxylate

生成物 1

HCID 18760281Ethyl 1-(3-(2-thienyl)propionyl)-3-piperidinecarboxylate収率 33.9%

試薬・触媒・溶媒 5

HCID 176Acetic Acid触媒HCID 24462Copper Sulfate触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Ethyl 1-(3-(2-thienyl)acrylyl)-3-piperidinecarboxylate (404.1 mg; 1.38 mmol) was suspended in dimethyl sulfoxide (8 ml). The suspension was treated with hydrazine hydrate (1.7 ml; 54.7 mmol), saturated aqueous copper sulfate solution (6 drops), and glacial acetic acid (6 drops). This mixture was then stirred at ambient temperature and sodium periodate (1.47 g; 6.87 mmol) in water (20 ml) was added dropwise. After stirring an additional 1 hour, the mixture was taken up between aqueous 5% sodium thiosulfate and dichloromethane. The dichloromethane was separated, dried with anhydrous potassium carbonate, and evaporated at ambient temperature under reduced pressure. The crude product was purified by reverse phase chromatography on a C18 column, eluting with 30:70 to 40:60 acetonitrile:water as a step gradient, giving ethyl 1-(3-(2-thienyl)propionyl)-3-piperidinecarboxylate (138 mg) as a colorless oil. MS m/z (positive ion) 296 (MH+; 100).

後処理

  1. stirringAfter stirring an additional 1 hour
  2. customThe dichloromethane was separated
  3. dry with materialdried with anhydrous potassium carbonate
  4. customevaporated at ambient temperature under reduced pressure
  5. customThe crude product was purified by reverse phase chromatography on a C18 column
  6. washeluting with 30:70 to 40:60 acetonitrile

出典と根拠

ORDレコード
ord-c9ef6bf1c6b34bffa857fab1fd4863ec
出典データセット
uspto-grants-2003_12
特許番号
US06664271B1

反応ノート

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