Dimethylformamide → 3-n-Heptyl-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 366534

반응식

HRID 366534 반응식
[H-].[Na+].[CH:3]12[CH2:8][CH:7]1[C:6](=[O:9])[NH:5][C:4]2=[O:10].I[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].CN(C)C=O>O1CCCC1.ClCCl>[CH2:12]([N:5]1[C:6](=[O:9])[CH:7]2[CH:3]([CH2:8]2)[C:4]1=[O:10])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 202741-IodoheptaneHCID 24758Sodium hydrideHCID 37200533-Azabicyclo[3.1.0]hexane-2,4-dione

생성물 1

HCID 232899803-n-Heptyl-3-azabicyclo[3.1.0]hexane-2,4-dione

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydride (0.11 g) was added to a solution of 3-azabicyclo[3.1.0]hexane-2,4-dione (0.3 g) in dry tetrahydrofuran (10 ml) under a nitrogen atmosphere at room temperature. The suspension was stirred for 5 minutes and 1-iodoheptane (0.61 g) was then added in one portion to the reaction mixture. After stirring for two hours at room temperature, dimethylformamide (5 ml) was added and the reaction mixture was stirred for a further 16 hours at room temperature. The reaction mixture was diluted with dichloromethane and then partitioned with water (20 ml). The aqueous phase was extracted with dichloromethane (20 ml) and the combined organic extracts were washed with water (2×20 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by chromatography on silica gel (50 g) using 25-30% ethyl acetate/hexane as eluant to give the title compound as a colourless oil.

후처리

  1. stirringAfter stirring for two hours at room temperature
  2. stirringthe reaction mixture was stirred for a further 16 hours at room temperature
  3. custompartitioned with water (20 ml)
  4. extractionThe aqueous phase was extracted with dichloromethane (20 ml)
  5. washthe combined organic extracts were washed with water (2×20 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by chromatography on silica gel (50 g)

출처 및 근거

ORD 기록
ord-d7033219963e47e58c27ef5289b19e91
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130241

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