Ammonia → Ethyl 1-(aminomethyl)cyclopentanecarboxylate

HRID 744913Notes

Reaction equation

HRID 744913 reaction equation
[C:1]([C:3]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].N>C(O)C.[Rh]>[NH2:2][CH2:1][C:3]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 15688760Ethyl 1-cyanocyclopentane-1-carboxylate

Product 1

HCID 21840386Ethyl 1-(aminomethyl)cyclopentanecarboxylate

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

20 g of ethyl 1-cyanocyclopentanecarboxylate are placed in 200 ml of a 10% solution of ammonia in ethanol and hydrogenated at 60° C. under a pressure of 100 bar in the presence of rhodium-on-alumina for 72 hours. After filtration on cellite® -- and evaporation, the residue is chromatographed on silica using a DCM/methanol/20% aqueous ammonia mixture (98/2/0.5; v/v/v) as the eluent.

Workup

  1. filtrationAfter filtration on cellite®
  2. customevaporation
  3. customthe residue is chromatographed on silica using a DCM/methanol/20% aqueous ammonia mixture (98/2/0.5

Sources & evidence

ORD record
ord-cb6df28a08d8447aa18bab6a19e46766
Source dataset
uspto-grants-1996_09
Patent number
US05559233

Reaction notes

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