4-tert-Butylbenzaldehyde → [Rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amine

HRID 855207

반응식

HRID 855207 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])=[CH:19][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])=[CH:19][CH:18]=2)[OH:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 703244-tert-ButylbenzaldehydeHCID 4124342-Amino-1-(4-chlorophenyl)ethan-1-olHCID 4311764Sodium borohydride

생성물 1

HCID 69342320[Rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amine

시약·촉매·용매 2

HCID 887Methanol용매HCID 22728543Water ethylacetate용매

실험 절차

1 ml of 4-tert-butylbenzaldehyde (6.15 mmol) and 960 mg of [rac]-2-amino-1-(4-chloro -phenyl)-ethanol (estimated 4.1 mmol) were dissolved in 40 ml methanol at rt, and after stirring for 5 min at rt, were refluxed for 2 h. After cooling down to rt, 310 mg (8.2 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 a small quantity of diethylether/heptane, filtered and the solid dried under high vacuo, leading to 723 g of [rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amine as a white solid (55%). MS (ISP) 318.2 (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 a small quantity of diethylether/heptane
  13. filtrationfiltered
  14. customthe solid dried under high vacuo

출처 및 근거

ORD 기록
ord-639939a6e94546d8a4bbb53f9d41552b
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259183B2

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