Methanesulfonyl chloride → 8-(5-Hexenyl)-8-azaspiro[4.5]decane-7,9-dione

HRID 741548

반응식

HRID 741548 반응식
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[CH2:8]1[C:12]2([CH2:17][C:16](=[O:18])[NH:15][C:14](=[O:19])[CH2:13]2)[CH2:11][CH2:10][CH2:9]1.CS(Cl)(=O)=O>C(N(CC)CC)C>[CH2:6]([N:15]1[C:14](=[O:19])[CH2:13][C:12]2([CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:17][C:16]1=[O:18])[CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1]

참가 물질

5

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 699635-Hexen-1-olHCID 1368438-Azaspiro(4.5)decane-7,9-dione

생성물 1

HCID 194266388-(5-Hexenyl)-8-azaspiro[4.5]decane-7,9-dione수율 13%

시약·촉매·용매 1

HCID 8471Triethylamine용매2회

실험 절차

A mixture of 5-hexen-1-ol (5 g) and 8-azaspiro[4.5]decane-7,9-dione (14 ml) in triethylamine (150 ml) was cooled on an ice bath. Methane-sulfonyl chloride (8.6 g) in triethylamine (50 ml) was added dropwise and the mixture was stirred at room temperature for 1 hour. The mixture was filtered off and the filtrate evaporated. Dichloromethane (7.7 g), potassium carbonate (7.6 g) and N,N-dimethylformamide (100 ml) were added to the residue and the mixture was stirred at 160° C. overnight. The mixture was filtered off and the filtrate evaporated. The residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 100/0 to 98/2). The pure fractions were collected and evaporated, yielding 1.5 g (13%) of 8-(5-hexenyl)-8-azaspiro[4.5]decane-7,9-dione (interm. 8).

후처리

  1. temperaturewas cooled on an ice bath
  2. filtrationThe mixture was filtered off
  3. customthe filtrate evaporated
  4. additionDichloromethane (7.7 g), potassium carbonate (7.6 g) and N,N-dimethylformamide (100 ml) were added to the residue
  5. stirringthe mixture was stirred at 160° C. overnight
  6. filtrationThe mixture was filtered off
  7. customthe filtrate evaporated
  8. customThe residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 100/0 to 98/2)
  9. customThe pure fractions were collected
  10. customevaporated

출처 및 근거

ORD 기록
ord-d19a713050324b19b29c9013d3276617
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05552399

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