Cyclopentanone → Ethyl 3-(cyclopentylamino)propanoate

HRID 2111245Notes

Reaction equation

HRID 2111245 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH2:8])[CH3:3].[C:10]1(=O)[CH2:14][CH2:13][CH2:12][CH2:11]1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH:8][CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)[CH3:3]

Participants

6

Reactant 4

HCID 8452CyclopentanoneHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 23053028Ethyl 3-(cyclopentylamino)propanoateYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 11.5 g (0.075 mole) of beta-alanine ethyl ester hydrochloride and 6.3 g (0.073 mole) of cyclopentanone in 200 mL of dichloromethane was added 6.5 g (0.082 mole) of sodium acetate and 22.5 g (0.107 mole) of sodium triacetoxyborohydride. The mixture was stirred 24 hours and then quenched by the addition of 200 mL of saturated sodium bicarbonate solution. After 20 minutes, the organic layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined dichloromethane layers were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to provide 12.0 g of 3-cyclopentylamino-propanoic acid ethyl ester, which was used without further purification.

Workup

  1. customquenched by the addition of 200 mL of saturated sodium bicarbonate solution
  2. waitAfter 20 minutes
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with dichloromethane
  5. dry with materialThe combined dichloromethane layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-593f7028fa3a491dba22058483a818fb
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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