alpha-Methylcinnamic acid → (R)-N-(1-Azabicyclo[2.2.2]oct-3-yl)(E-2-methyl-3-phenylpropenamide)

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.[CH3:12]/[C:13](=[CH:17]\[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)/[C:14](O)=[O:15]>>[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH:11][C:14](=[O:15])/[C:13](/[CH3:12])=[CH:17]/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:4]2

Participants

Reactant 2

HCID 637817alpha-Methylcinnamic acid

HCID 12494972(R)-(+)-3-Aminoquinuclidine Dihydrochloride

Product 1

HCID 20613749(R)-N-(1-Azabicyclo[2.2.2]oct-3-yl)(E-2-methyl-3-phenylpropenamide)

Procedure

Prepared as 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-2-methyl-3-phenylpropenoic acid; MS (ES+) 271 (MH+).

Workup

customPrepared as free base by a method analogous to

Sources & evidence

ORD record: ord-713c544b5aed4944943cf80d81728db1
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06683090B1

Reaction notes

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