Ethanol → HCID 67759045, 화합물

HRID 356107

반응식

HRID 356107 반응식
[N:1]12[CH2:9][CH:5]([CH2:6][CH2:7][CH2:8]1)[C:4](=O)[CH2:3][CH2:2]2.C1(C)C=CC(S([CH2:20][N+:21]#[C-])(=O)=O)=CC=1.C(O)C.CC(C)([O-])C.[K+]>C(COC)OC>[N:1]12[CH2:9][C@H:5]([CH2:6][CH2:7][CH2:8]1)[C@H:4]([C:20]#[N:21])[CH2:3][CH2:2]2

참가 물질

6

반응물 4

HCID 702EthanolHCID 161915Tosylmethyl isocyanideHCID 4178971-Azabicyclo(3.3.1)nonan-4-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 67759045HCID 67759045, 화합물수율 46.8%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
5 °C

실험 절차

To a solution of 2.00 g of 1-azabicyclo[3.3.1]nonan-4-one in 100 ml of dimethoxyethane, 3.65 g of p-toluenesulfonylmethylisocyanide and 1.13 g of ethanol were added, followed by cooling to 5° C. Then, 4.00 g of potassium tert-butoxide was added while keeping the internal temperature below 10° C. The mixture was stirred at room temperature for 30 minutes, followed by further stirring at 40° C. for 30 minutes. The precipitate thus formed was removed by filtration. The residue obtained by evaporation of the solvent was purified by an alumina column chromatography (eluent: chloroform:hexane=1:1). The resulting crude product was then purified by silica gel column chromatography (eluent: chloroform:methanol=20:1), whereby 1.01 g of (4R*,5R*)-1-azabicyclo[3.3.1]nonane-4-carbonitrile was obtained.

후처리

  1. customthe internal temperature below 10° C
  2. stirringby further stirring at 40° C. for 30 minutes
  3. customThe precipitate thus formed
  4. customwas removed by filtration
  5. customThe residue obtained by evaporation of the solvent
  6. customwas purified by an alumina column chromatography (eluent: chloroform:hexane=1:1)
  7. customThe resulting crude product was then purified by silica gel column chromatography (eluent: chloroform:methanol=20:1)

출처 및 근거

ORD 기록
ord-2e57fe313bf04f39bdf3ad8a3c083277
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834499

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