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

HRID 518862
ノート
印刷プレビュー

反応式

HRID 518862 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 177Acetaldehyde2 回HCID 5049666Sodium triacetoxyborohydrideHCID 866980147-(3-Isopropoxy-4-nitrophenyl)-1,7-diazaspiro[4.4]nonane

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5885577c1158452bbed779ce170c71d2
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09115140B2

反応ノート

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