1,1'-Azobis(cyclohexanecarbonitrile) → 1-Methanesulfonyl-5-chloro-spiro[indoline-3,3'-pyrrolidine]

HRID 83984

반응식

HRID 83984 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:13][C:14](=[CH2:20])[CH2:15][CH2:16][N:17]=[N+]=[N-])[S:9]([CH3:12])(=[O:11])=[O:10])=[C:4](I)[CH:3]=1.C[Si]([SiH]([Si](C)(C)C)[Si](C)(C)C)(C)C.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>C1C=CC=CC=1>[CH3:12][S:9]([N:8]1[C:5]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:14]2([CH2:15][CH2:16][NH:17][CH2:20]2)[CH2:13]1)(=[O:11])=[O:10]

참가 물질

5

반응물 3

HCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 123134Tris(trimethylsilyl)silaneHCID 86627362N-(4-Chloro-2-iodo-phenyl)-N-(4-azido-2-methylene-butyl)-methanesulfonamide

생성물 1

HCID 581373391-Methanesulfonyl-5-chloro-spiro[indoline-3,3'-pyrrolidine]수율 85.3%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A degassed solution of N-(4-Chloro-2-iodo-phenyl)-N-(4-azido-2-methylene-butyl)-methanesulfonamide (1.38 g) in benzene (200 ml) was heated to reflux under argon. Tris(trimethylsilyl)silane (1.32 ml) was added dropwise followed by 1,1′-azobis(cyclohexane carbonitrile) (110 mg). The reaction mixture was stirred at reflux for 20 hours then concentrated in vacuo. The residue was dissolved in ethyl acetate (60 ml), extracted with HC12N (3×60 ml). The aqueous layer was basified with 2N sodium hydroxide (250 ml) then extracted with ethyl acetate (3×150 ml). The combined organic layers were dried over sodium sulfate and the solvent evaporated in vacuo to afford 1-methanesulfonyl-5-chloro-spiro[indoline-3,3′-pyrrolidine] (766 mg) which was used as such for the next step.

후처리

  1. temperatureto reflux under argon
  2. temperatureat reflux for 20 hours
  3. concentrationthen concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (60 ml)
  5. extractionextracted with HC12N (3×60 ml)
  6. extractionthen extracted with ethyl acetate (3×150 ml)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. customthe solvent evaporated in vacuo

출처 및 근거

ORD 기록
ord-bc70f85125c042febb33b40f444865ce
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846907B2

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