(2E)-3-(furan-3-yl)prop-2-enoic acid → (R)-N-(1-Azabicyclo[2.2.2]oct-3-yl)[E-3-(3-furyl)propenamide]

HRID 1840910Notes

Reaction equation

HRID 1840910 reaction equation
Cl.Cl.[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH2:11])[CH2:4]2.[O:12]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19](O)=[O:20])=[CH:13]1>>[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH:11][C:19](=[O:20])/[CH:18]=[CH:17]/[C:14]1[CH:15]=[CH:16][O:12][CH:13]=1)[CH2:4]2

Participants

3

Reactant 2

HCID 643403(2E)-3-(furan-3-yl)prop-2-enoic acidHCID 12494972(R)-(+)-3-Aminoquinuclidine Dihydrochloride

Product 1

HCID 20613738(R)-N-(1-Azabicyclo[2.2.2]oct-3-yl)[E-3-(3-furyl)propenamide]

Procedure

Prepared as a free base by a method analogous to that described in Example 1 from (R)-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride and E-3-(3-furyl)propenoicacid; the compound was purified by chromatography on silica gel using ammoniated methanol/chloroform mixtures as the eluent; MS (ES+) 247 (MH+).

Workup

  1. customPrepared as a free base by a method analogous to
  2. customthe compound was purified by chromatography on silica gel using ammoniated methanol/chloroform mixtures as the eluent

Sources & evidence

ORD record
ord-9b84b846de394e5eb1247f8c422a2dd1
Source dataset
uspto-grants-2004_01
Patent number
US06683090B1

Reaction notes

Loading…