Ammonia → 1-[1-(4-Chlorophenyl)cyclobutyl]-3-ethyl-1-iminopentan-3-ol

HRID 728277ノート

反応式

HRID 728277 の反応式
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:14](=[N:22]O)[CH2:15][C:16]([CH2:20][CH3:21])([OH:19])[CH2:17][CH3:18])[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.O.N>COCCOC.[Ti](Cl)(Cl)(Cl)Cl>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:14](=[NH:22])[CH2:15][C:16]([CH2:20][CH3:21])([OH:19])[CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13]2)=[CH:8][CH:9]=1

参加物

7

反応物 4

HCID 222AmmoniaHCID 962WaterHCID 4311764Sodium borohydrideHCID 867439391-[1-(4-Chlorophenyl)cyclobutyl]-3-ethyl-3-hydroxypentan-1-one oxime

生成物 1

HCID 198237421-[1-(4-Chlorophenyl)cyclobutyl]-3-ethyl-1-iminopentan-3-ol

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
0 °C

実験手順

Titanium (IV) chloride (3.9 ml) was added dropwise to stirred dry 1,2-dimethoxyethane (68 ml) cooled to 0° C. under nitrogen. The temperature was maintained at 0° C. and powdered sodium borohydride (2.7 g) was added. A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-3-ethyl-3-hydroxypentan-1-one oxime (5.2 g) in dry 1,2-dimethoxyethane (17 ml) was then added dropwise under nitrogen and the mixture stirred for 30 minutes at 0° C. and then at ambient temperature for 14 hours. After cooling the mixture to 0° C., water (170 ml) was added dropwise and the mixture basified with aqueous ammonia solution (S.G. 0.880) with cooling. The resulting solution was extracted with ether and the extracts washed with brine and dried. Removal of the solvents by evaporation in vacuo gave an oil which was distilled (b.p. 150/0.05 mm) to give 1-[1-(4-chlorophenyl)cyclobutyl]-3-ethyl-1-iminopentan-3-ol.

後処理

  1. temperatureThe temperature was maintained at 0° C.
  2. waitat ambient temperature for 14 hours
  3. temperatureAfter cooling the mixture to 0° C.
  4. temperaturewith cooling
  5. extractionThe resulting solution was extracted with ether
  6. washthe extracts washed with brine
  7. customdried
  8. customRemoval of the solvents
  9. customby evaporation in vacuo
  10. customgave an oil which
  11. distillationwas distilled (b.p. 150/0.05 mm)

出典と根拠

ORDレコード
ord-5f3d7908594d472cb1b9352b1e97385d
出典データセット
uspto-grants-1991_09
特許番号
US05047432

反応ノート

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