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

HRID 1173299Notes

Reaction equation

HRID 1173299 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-a22a27862ef14d7caa6991d78aa99e75
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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