Cyclopentylamine → Methyl 3-(cyclopentylamino)-2-methylpropanoate

HRID 2111240Notes

Reaction equation

HRID 2111240 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]([O:12][CH3:13])(=[O:11])[C:8]([CH3:10])=[CH2:9]>CO>[CH3:13][O:12][C:7](=[O:11])[CH:8]([CH3:10])[CH2:9][NH:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 6658Methyl Methacrylate

Product 1

HCID 43398438Methyl 3-(cyclopentylamino)-2-methylpropanoateYield 82.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 42.575 g (0.50 mole) of cyclopentylamine (Aldrich), 60.072 g (0.60 mole) of methyl methacrylate (Aldrich) and 250 mL of methanol was heated at reflux under an argon atmosphere for 29 hours, then ca 250 mL of solvent was distilled out at atmospheric pressure. The residue was distilled under vacuum (11 mm Hg, bp 114-116 degrees) to give 76.570 g (82%) of (rac)-3-cyclopentylamino-2-methyl-propanoic acid methyl ester.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under an argon atmosphere for 29 hours
  3. distillationca 250 mL of solvent was distilled out at atmospheric pressure
  4. distillationThe residue was distilled under vacuum (11 mm Hg, bp 114-116 degrees)

Sources & evidence

ORD record
ord-c87a50146af046eabd83f637f2864bff
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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