Cyclopentanone → Methyl 3-(cyclopentylamino)propanoate

HRID 2279994Notes

Reaction equation

HRID 2279994 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 dissolved in DCM (200 mL). Cyclopentanone (6.43 mL, 0.07 mol, 0.77 eq), sodium acetate (5.96 g, 0.07 mol, 0.77 eq) and sodium triacetoxyborohydride (22 g, 0.10 mol, 1.11 eq) were added then the reaction was stirred at rt for 16h. 20% Sodium bicarbonate (100 mL) and 2 M sodium hydroxide (50 mL) were added and the product extracted using DCM/H2O. The organic extracts were combined, washed with sat. NaCl, dried (MgSO4) and evaporated under reduced pressure 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. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4026d7cfdad644d698aad162e9cec367
Source dataset
uspto-grants-2015_09
Patent number
US09133199B2

Reaction notes

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