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

HRID 432808노트

반응식

HRID 432808 반응식
[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]

참가 물질

10

반응물 4

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

생성물 1

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

시약·촉매·용매 5

HCID 176Acetic Acid촉매HCID 24462Copper Sulfate촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c9ef6bf1c6b34bffa857fab1fd4863ec
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664271B1

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