Cyclopentanone → Methyl 3-(cyclopentylamino)propanoate

HRID 1044073Notes

Reaction equation

HRID 1044073 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].[C:8]1(=O)[CH2:12][CH2:11][CH2:10][CH2:9]1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(Cl)Cl>[CH:8]1([NH:1][CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

8

Reactant 6

HCID 8452CyclopentanoneHCID 14798Sodium HydroxideHCID 192794Methyl beta-alanateHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 28307099Methyl 3-(cyclopentylamino)propanoateYield 74.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3-aminopropanoate (9.37 g, 0.09 mol) was solubilised in DCM (200 ml) and cyclopentanone (6.43 ml, 0.07 mol), sodium acetate (5.96 g, 0.07 mol) and sodium triacetoxyborohydride (22 g, 0.10 mol) were added. The reaction was stirred at rt for 16 h. 20% sodium bicarbonate (100 ml) and 2M sodium hydroxide (50 ml) were then added and the product extracted using DCM/H2O. The organic extracts were combined, washed with sat NaCl, dried using MgSO4, filtered and the filtrate evaporated under reduced pressure and further dried in vacuo to give the product as a pale yellow oil (8.90 g, 55%); MS+ve: 172.4.

Workup

  1. extractionthe product extracted
  2. washwashed with sat NaCl
  3. customdried
  4. filtrationfiltered
  5. customthe filtrate evaporated under reduced pressure
  6. customfurther dried in vacuo

Sources & evidence

ORD record
ord-8117cbf099634e9eacc3174117768e26
Source dataset
uspto-grants-2013_10
Patent number
US08563542B2

Reaction notes

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