2,4-Dimethoxybenzylamine → 4-Tert-butyl 2-methyl 2-((2,4-dimethoxybenzylamino)methyl)morpholine-2,4-dicarboxylate

HRID 1618962Notes

Reaction equation

HRID 1618962 reaction equation
S(O[CH2:12][C:13]1([C:26]([O:28][CH3:29])=[O:27])[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1)(C1C=CC(C)=CC=1)(=O)=O.[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=1[CH2:40][NH2:41]>C(#N)C>[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=1[CH2:40][NH:41][CH2:12][C:13]1([C:26]([O:28][CH3:29])=[O:27])[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:14]1

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 866714174-Tert-butyl 2-methyl 2-(tosyloxymethyl)morpholine-2,4-dicarboxylate

Product 1

HCID 672283494-Tert-butyl 2-methyl 2-((2,4-dimethoxybenzylamino)methyl)morpholine-2,4-dicarboxylateYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

E4 (365 mg, 0.850 mmol) was dissolved in acetonitrile (10 mL), (2,4-dimethoxyphenyl)methanamine (700 μL, 4.66 mmol) was added and the solution was stirred for 15 h at reflux temperature. The reaction mixture was concentrated in vacuo, extracted with water/EtOAc and washed twice with water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography from toluene:EtOAc 100:0 to 20:80 which gave the title compound (115 mg, 32%). MS (ES) C21H32N2O7 requires: 424. found: 425.2 [M+H]+.

Workup

  1. temperatureat reflux temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionextracted with water/EtOAc
  4. washwashed twice with water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography from toluene:EtOAc 100:0 to 20:80 which

Sources & evidence

ORD record
ord-3c5e3878957b44d0aa041f3b283599cb
Source dataset
uspto-grants-2014_07
Patent number
US08772286B2

Reaction notes

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