Methylamine → 3,5-Di-tert-butyl-2-[(methylamino)methyl]phenol

HRID 1173304Notes

Reaction equation

HRID 1173304 reaction equation
[C:1]([C:5]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[C:9]([OH:17])[C:6]=1[CH:7]=O)([CH3:4])([CH3:3])[CH3:2].[CH3:18][NH2:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(O)(=O)C>[C:1]([C:5]1[C:6]([CH2:7][NH:19][CH3:18])=[C:9]([OH:17])[CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 128155852,4-Di-tert-butyl-6-hydroxybenzaldehyde

Product 1

HCID 101061223,5-Di-tert-butyl-2-[(methylamino)methyl]phenol

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.234 g (1.00 mmol) of the product of Step A, 3 mL of 2 N methylamine in TMF, and 0.5 mL acetic acid dissolved in 4.0 mL 1,2-dichloroethane was stirred at room temperature for 5 h. Sodium triacetoxyborohydride (0.422 g; 2.0 mmol) and 10 mL of 1,2-dichloroethane was then added and the resulting mixture was stirred overnight at room temperature. The reaction mixture was then treated with excess saturated aqueous NaHCO3. The aqueous layer was separated and extracted with CH2Cl2, the organic layers were combined, dried (Na2SO4), filtered, and evaporated. The residue was purified on a silica gel flash chromatography column eluted with CH2Cl2-MeOH—NH4OH (95:5:0.5). Evaporation of the purified fractions and drying in vacuo afforded the title compound. HPLC/MS: 250.2 (M+1); Rt=2.5 min.

Workup

  1. stirringthe resulting mixture was stirred overnight at room temperature
  2. customThe aqueous layer was separated
  3. extractionextracted with CH2Cl2
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on a silica gel flash chromatography column
  8. washeluted with CH2Cl2-MeOH—NH4OH (95:5:0.5)
  9. customEvaporation of the purified fractions
  10. customdrying in vacuo

Sources & evidence

ORD record
ord-7640d17cec0c418f889a6b83c377cfc4
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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