Methanol → HCID 67125477, compound

HRID 1617317Notes

Reaction equation

HRID 1617317 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][O-:12].[Na+].[CH3:14][OH:15]>ClCCl>[CH3:11][O:12][C:14](=[O:15])[NH:10][C@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamineHCID 10942334Sodium Methoxide

Product 1

HCID 67125477HCID 67125477, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17.2 g (105 mmol) CDT are added to a mixture of 20.0 g (100 mmol) (S)-1-(4-bromophenyl)-ethylamine and 17.6 mL (125 mmol) TEA in 300 mL dichloromethane at 0° C. Stirring is continued for 15 min at 5° C. After that time, the solvent is removed in vacuo and taken up in 50 mL methanol. 33.4 mL (180 mmol) sodium methoxide in methanol (30%) are added and stirring is continued for 48 h at rt. After that time, the solvent is removed in vacuo, the residue is taken up in ethyl acetate and washed with sat. KHSO4-solution (2×) and water. The organic layer is dried over magnesium sulphate and the solvent is removed by evaporation.

Workup

  1. customAfter that time, the solvent is removed in vacuo
  2. stirringstirring
  3. waitis continued for 48 h at rt
  4. customAfter that time, the solvent is removed in vacuo
  5. washwashed with sat. KHSO4-solution (2×) and water
  6. dry with materialThe organic layer is dried over magnesium sulphate
  7. customthe solvent is removed by evaporation

Sources & evidence

ORD record
ord-53aa2eab0e7b4121908fe910c720fe2a
Source dataset
uspto-grants-2014_07
Patent number
US08765959B2

Reaction notes

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