Ammonia → Ethyl 1-(aminomethyl)cyclopentanecarboxylate

HRID 326761Notes

Reaction equation

HRID 326761 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
  2. customon cellite® and evaporation
  3. customthe residue is chromatographed on silica using a DCM/methanol/20% aqueous ammonia mixture (98/2/0.5

Sources & evidence

ORD record
ord-e60940f48eaf47bcac149a78af98be09
Source dataset
uspto-grants-1993_12
Patent number
US05270317

Reaction notes

Loading…