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

HRID 855205

반응식

HRID 855205 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 22728543Water ethylacetate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-63c2ce4cffdd4d1798b27f8886e72570
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259183B2

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