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

HRID 1494147Notes

Reaction equation

HRID 1494147 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) until theoretical uptake of hydrogen (4 moles) for saturation of the nitrile and double bond is obtained (about 12 hours). 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 hours)
  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-c7622d67448f443b8d9874d5faf2ea2f
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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