alpha-(Aminomethyl)-3,4-dichlorobenzenemethanol → 2-{[(4-tert-Butylphenyl)methyl]amino}-1-(3,4-dichlorophenyl)ethan-1-ol

HRID 855205

反応式

HRID 855205 の反応式
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:13][CH2:14][CH:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)[OH:16].[BH4-].[Na+]>CO.O.CCOC(C)=O>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:13][CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[OH:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 19349alpha-(Aminomethyl)-3,4-dichlorobenzenemethanolHCID 703244-tert-ButylbenzaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 693423572-{[(4-tert-Butylphenyl)methyl]amino}-1-(3,4-dichlorophenyl)ethan-1-ol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 22728543Water ethylacetate溶媒

実験手順

0.32 ml of 4-tert-butylbenzaldehyde (1.8 mmol) and 250 mg of [rac]-2-amino-1-(3,4-dichloro -phenyl)-ethanol (1.2 mmol) were dissolved in 10 ml methanol at rt, and after stirring for 5 min at rt, were refluxed for 2 h. After cooling down to rt, 68 mg (1.8 mmol) of sodium borohydride were added and after stirring for 15 min at rt, the reaction mixture was then refluxed for 2 h. After cooling down to rt, the residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue was stirred with diethylether/heptane, filtered and the solid dried under high vacuo, leading to 147 mg of [rac]-(4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-amine as a light yellow solid (35%). MS (ISP) 352.3 (M+H)+.

後処理

  1. temperaturewere refluxed for 2 h
  2. temperatureAfter cooling down to rt
  3. stirringafter stirring for 15 min at rt
  4. temperaturethe reaction mixture was then refluxed for 2 h
  5. temperatureAfter cooling down to rt
  6. customAfter separation of the organic phase
  7. extractionthe aqueous phase was extracted with EtOAc
  8. washthe combined organic phases were washed with brine
  9. dry with materialdried with magnesium sulfate
  10. filtrationfiltered off
  11. concentrationconcentrated in vacuo
  12. stirringThe residue was stirred with diethylether/heptane
  13. filtrationfiltered
  14. customthe solid dried under high vacuo

出典と根拠

ORDレコード
ord-63c2ce4cffdd4d1798b27f8886e72570
出典データセット
uspto-grants-2007_08
特許番号
US07259183B2

関連ノート

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