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

HRID 1173299ノート

反応式

HRID 1173299 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a22a27862ef14d7caa6991d78aa99e75
出典データセット
uspto-grants-2010_11
特許番号
US07834062B2

反応ノート

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