Ethyl 4-(3-cyanopropyl)-7-(3-pyridyl)-6-heptenoate → Ethyl 8-amino-4-[3-(3-pyridyl)propyl]-octanoate

HRID 465608Notes

Reaction equation

HRID 465608 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH:6]([CH2:14][CH:15]=[CH:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:2].[H][H]>N.C1(C)C=CC=CC=1.[Rh]>[NH2:2][CH2:1][CH2:3][CH2:4][CH2:5][CH:6]([CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 2

HCID 54476179Ethyl 4-(3-cyanopropyl)-7-(3-pyridyl)-6-heptenoateHCID 178418361HCID 178418361, compound

Product 1

HCID 14986702Ethyl 8-amino-4-[3-(3-pyridyl)propyl]-octanoate

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 222AmmoniaSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of 125 g of ethyl 4-(3-cyanopropyl)-7-(3-pyridyl)-6-heptenoate in 825 ml of 9.53% ethanolic ammonia is added to a slurry of 62.5 g of 5% rhodium on carbon (50% water wet) in 300 ml of 9.53% ethanolic ammonia. The mixture is hydrogenated at about 3 atmospheres pressure (50 psi=3.45 bar) until theoretical uptake of hydrogen (4 moles) for saturation of the nitrile and double bond is obtained (about 12 h). The catalyst is then filtered off, washed with methylene chloride and ethanol, and the filtrate is evaporated to dryness to yield a residue which is redissolved in toluene. Evaporation to dryness yields ethyl 8-amino-4-[3-(3-pyridyl)propyl]-octanoate.

Workup

  1. customdouble bond is obtained (about 12 h)
  2. filtrationThe catalyst is then filtered off
  3. washwashed with methylene chloride and ethanol
  4. customthe filtrate is evaporated to dryness
  5. customto yield a residue which
  6. customEvaporation to dryness

Sources & evidence

ORD record
ord-c5227cc310c54afcb60b93c9663a4fe1
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

Loading…