Cyclopentanone → N-Cyclopentyl-amino-acetic acid ethyl ester hydrochloride

HRID 2418183Notes

Reaction equation

HRID 2418183 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:7].[CH2:8]([O:10][C:11](=[O:14])[CH2:12][NH2:13])[CH3:9].C([BH3-])#N.[Na+]>CO>[ClH:7].[CH2:8]([O:10][C:11](=[O:14])[CH2:12][NH:13][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:9]

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 13089663N-Cyclopentyl-amino-acetic acid ethyl ester hydrochlorideYield 51.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclopentanone (10 g) and glycine ethyl ester hydrochloride (21.6 g) are dissolved in 200 ml of methanol, and 7.48 g of sodium cyanoborohydride is added in small portions with stirring at room temperature. The mixture is further stirred at room temperature for 3 hours and the reaction mixture is concentrated under reduced pressure. To the residue is added 500 ml of water and the mixture is adjusted to pH 10 with diluted sodium hydroxide solution and extracted with 300 ml of ethyl acetate. The extract is washed with saturated aqueous sodium chloride and dried over sodium sulfate. The solvent is then distilled off under reduced pressure and the resulting oily product is dissolved in 200 ml of ether, followed by addition of 10 ml of 10% alcoholic hydrochloride, whereupon crystals immediately separates out. The crystals are collected by filtration to give 12.7 g of N-cyclopentylglycine ethyl ester hydrochloride as colorless needles melting at 174°-175° C.

Workup

  1. stirringThe mixture is further stirred at room temperature for 3 hours
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. additionTo the residue is added 500 ml of water
  4. extractionextracted with 300 ml of ethyl acetate
  5. washThe extract is washed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent is then distilled off under reduced pressure
  8. dissolutionthe resulting oily product is dissolved in 200 ml of ether
  9. additionfollowed by addition of 10 ml of 10% alcoholic hydrochloride, whereupon crystals
  10. filtrationThe crystals are collected by filtration

Sources & evidence

ORD record
ord-6e08d5c3989249b3aabfdbbc3904e56a
Source dataset
uspto-grants-1984_09
Patent number
US04472383

Reaction notes

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