Methanol → 2-(2-Amino-5-methylcyclohexyl)acetic acid

HRID 1614224Notes

Reaction equation

HRID 1614224 reaction equation
S(Cl)(Cl)=[O:2].[C:5]([CH:8]1[CH2:13][CH:12]([CH3:14])[CH2:11][CH2:10][CH:9]1[NH2:15])(O)=O.[CH3:16][OH:17]>>[C:16]([CH2:5][CH:8]1[CH2:13][CH:12]([CH3:14])[CH2:11][CH2:10][CH:9]1[NH2:15])([OH:2])=[O:17]

Participants

4

Reactant 3

HCID 887Methanol3×HCID 24386Thionyl Chloride2×HCID 149939762-Carboxy-4-methylcyclohexan-1-yl-amine

Product 1

HCID 199303132-(2-Amino-5-methylcyclohexyl)acetic acidYield 85%

Procedure

7.3 ml (0.1 mol) of thionyl chloride are added to 30 ml of methanol at -5° C. under N2, and 15 g (0.096 mol) of 2-carboxy-4-methylcyclohexan-1-yl-amine in 10 ml of methanol are then added dropwise to this solution at 0° C. After the mixture ha been stirred under reflux for 12 hours it is cooled, a further 10 ml of methanol and 3 ml (0.04 mol) of thionyl chloride are added, and stirring under reflux is continued for 4 hours. After cooling and evaporation to dryness, 5 g of the residue is taken up in about 50 ml of diethyl ether and the mixture is washed in about 100 ml of cold 1N Naton lye and water. The organic phase is dried and concentrated. 3.5 g (85% of theory) of 2-carboxymethyl-4-methyl-cyclohexan-1-yl-amine are obtained as a pale yellow oil.

Workup

  1. temperatureunder reflux for 12 hours it
  2. temperatureis cooled
  3. stirringstirring
  4. temperatureunder reflux
  5. temperatureAfter cooling
  6. customevaporation to dryness, 5 g of the residue
  7. washthe mixture is washed in about 100 ml of cold 1N Naton lye and water
  8. customThe organic phase is dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e454255c0e9f456d9b803b6ce1fc4a26
Source dataset
uspto-grants-1993_03
Patent number
US05196441

Reaction notes

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