Di-tert-butyl dicarbonate → [2-(3,4-Dimethoxy-phenyl)-1-methyl-ethyl]-ethyl amine

HRID 1828970

Reaction equation

HRID 1828970 reaction equation
Br.[CH2:2]([NH:4][CH:5]([CH3:15])[CH2:6][C:7]1[CH:8]=[C:9]([OH:14])[C:10]([OH:13])=[CH:11][CH:12]=1)[CH3:3].[C:16](=[O:19])(O)[O-].[Na+].[C:21](O[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(OC(C)(C)C)=O>O.C1COCC1>[CH3:21][O:14][C:9]1[CH:8]=[C:7]([CH2:6][CH:5]([NH:4][CH2:2][CH3:3])[CH3:15])[CH:12]=[CH:11][C:10]=1[O:19][CH3:16].[C:32]([O:31][C:29](=[O:30])[N:4]([CH:5]([CH3:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([OH:14])[CH:8]=1)[CH2:2][CH3:3])([CH3:33])([CH3:34])[CH3:35]

Participants

7

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 1303564-(2-(Ethylamino)propyl)-1,2-benzenediol hydrobromideHCID 516892Sodium Bicarbonate

Product 2

HCID 22061570[2-(3,4-Dimethoxy-phenyl)-1-methyl-ethyl]-ethyl amineHCID 70986816HCID 70986816, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To all of 2B from the above reaction mixture was added 30 mL of 50% THF in water. To the reaction mixture 1.1 g of sodium bicarbonate was added as a solid followed by 1.35 g (6.18 mmol) of di-t-butyl dicarbonate in 7 mL of THF dropwise over a period of 30 minutes. The reaction mixture was allowed to stir at room temperature for 18 hours, then concentrated under reduced pressure. This was diluted with 50 mL of water and the pH of the solution was adjusted to 5. The aqueous layer was extracted with 3×100 mL of ethyl acetate. The organic layers were combined, dried (anhydrous Na2SO4) and concentrated to dryness. The residue was purified by silica gel column chromatography using 30% ethyl acetate in hexane to give 764 mg (2.58 mmol, 53% from 2A) of 2C as a clear gum (M+Na, 318).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThis was diluted with 50 mL of water
  3. extractionThe aqueous layer was extracted with 3×100 mL of ethyl acetate
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-802761843dd144eb8064b37e4406bdcd
Source dataset
uspto-grants-2006_06
Patent number
US07060847B2

Linked notes

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