Propylamine → 5-tert-Butyl-2-[(propylamino)methyl]phenol

HRID 1173299노트

반응식

HRID 1173299 반응식
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[C:7]([OH:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:14]([NH2:17])[CH2:15][CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:17][CH2:14][CH2:15][CH3:16])=[C:7]([OH:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 7852PropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 137652724-tert-Butyl-2-hydroxybenzaldehyde

생성물 1

HCID 103311045-tert-Butyl-2-[(propylamino)methyl]phenol

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매2회

실험 절차

To a mixture of 0.178 g (0.1 mmol) of the product of Step A and 0.206 g (3.5 mmol) of n-propylamine dissolved in 10 mL of CH2Cl2 was added 0.5 g of finely powdered 4 Å molecular sieves. The reaction mixture was stirred under a nitrogen atmosphere at room temperature overnight, then 0.53 g (2.5 mmol) of sodium triacetoxyborohydride was added. The reaction was then stirred an addition 8 h at room temperature, then diluted with CH2Cl2 and MeOH. The mixture was filtered through a pad of Celite filter aid eluted with CH2Cl2, and the filtrate was washed with saturated aqueous NaHCO3. The organic layer was the separated, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on a flash chromatography column eluted with CH2Cl2-MeOH—NH4OH (95:4:1) to afford the title compound.

후처리

  1. additionwas added 0.5 g of finely powdered 4 Å molecular sieves
  2. stirringThe reaction was then stirred
  3. additionan addition 8 h at room temperature
  4. filtrationThe mixture was filtered through a pad of Celite
  5. filtrationfilter aid
  6. washeluted with CH2Cl2
  7. washthe filtrate was washed with saturated aqueous NaHCO3
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe residue was purified on a flash chromatography column
  12. washeluted with CH2Cl2-MeOH—NH4OH (95:4:1)

출처 및 근거

ORD 기록
ord-a22a27862ef14d7caa6991d78aa99e75
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834062B2

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