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

HRID 22424Notes

Reaction equation

HRID 22424 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 has 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-8659bf8736824490a710be0d0840ed30
Source dataset
uspto-grants-1995_06
Patent number
US05428073

Reaction notes

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