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Acetaldehyde → 1-Ethyl-7-[4-nitro-3-(propan-2-yloxy)phenyl]-1,7-diazaspiro[4.4]nonane

HRID 518862
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HRID 518862 반응식
[CH:1](=O)[CH3:2].[N+:4]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:21][CH2:20][C:15]3([NH:19][CH2:18][CH2:17][CH2:16]3)[CH2:14]2)=[CH:9][C:8]=1[O:22][CH:23]([CH3:25])[CH3:24])([O-:6])=[O:5].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CCOCC>[CH2:1]([N:19]1[C:15]2([CH2:20][CH2:21][N:13]([C:10]3[CH:11]=[CH:12][C:7]([N+:4]([O-:6])=[O:5])=[C:8]([O:22][CH:23]([CH3:25])[CH3:24])[CH:9]=3)[CH2:14]2)[CH2:16][CH2:17][CH2:18]1)[CH3:2]
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참가 물질

5

반응물 3

HCID 177Acetaldehyde2회HCID 5049666Sodium triacetoxyborohydrideHCID 866980147-(3-Isopropoxy-4-nitrophenyl)-1,7-diazaspiro[4.4]nonane

생성물 1

HCID 866980151-Ethyl-7-[4-nitro-3-(propan-2-yloxy)phenyl]-1,7-diazaspiro[4.4]nonane

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

1.0 ml of acetaldehyde is added to a solution of 500 mg of 7-[4-nitro-3-(propan-2-yloxy)phenyl]-1,7-diazaspiro[4.4]nonane in 20 ml of 1,4-dichloroethane, cooled in a bath of ice-cold water. After 30 minutes, 1.12 g of sodium triacetoxyborohydride are added in small portions and the mixture is left to return to ambient temperature. The mixture is stirred at ambient temperature for 15 hours. 1 ml of acetaldehyde is then added and the mixture is stirred for 7 h. The mixture is concentrated to dryness under reduced pressure and the residue is diluted in 100 ml of dichloromethane. The organic phase is washed three times with 50 ml of water and the organic phase is dried over anhydrous magnesium sulfate, filtered and then concentrated to dryness under reduced pressure. The residue is purified by chromatography on silica gel, elution being carried out with a dichloromethane/isopropanol gradient: 100/0 to 50/50, and then by further chromatography on silica gel, elution being carried out with a dichloromethane/acetone gradient: 100/0 to 50/50, so as to obtain a yellow oil. This oil is taken up with ether, and the precipitate obtained is filtered off. The filtrate is concentrated to dryness under reduced pressure, so as to give 250 mg of 1-ethyl-7-[4-nitro-3-(propan-2-yloxy)phenyl]-1,7-diazaspiro[4.4]nonane in the form of a yellow oil.

후처리

  1. temperaturecooled in a bath of ice-cold water
  2. waitthe mixture is left
  3. customto return to ambient temperature
  4. stirringthe mixture is stirred for 7 h
  5. concentrationThe mixture is concentrated to dryness under reduced pressure
  6. additionthe residue is diluted in 100 ml of dichloromethane
  7. washThe organic phase is washed three times with 50 ml of water
  8. dry with materialthe organic phase is dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure
  11. customThe residue is purified by chromatography on silica gel, elution
  12. wash100/0 to 50/50, and then by further chromatography on silica gel, elution
  13. custom100/0 to 50/50, so as to obtain a yellow oil
  14. customthe precipitate obtained
  15. filtrationis filtered off
  16. concentrationThe filtrate is concentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-5885577c1158452bbed779ce170c71d2
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115140B2

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