Dichloromethane → Imidazole-1-carboxylic acid 1-azabicyclo[2.2.2]oct-3-yl ester

HRID 271313Notes

Reaction equation

HRID 271313 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[C:10](N1C=CN=C1)([N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)=[O:11].C(Cl)Cl>ClCCCl>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10]([N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)=[O:11])[CH2:2]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 15381(+-)-3-QuinuclidinolHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 59835690Imidazole-1-carboxylic acid 1-azabicyclo[2.2.2]oct-3-yl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

According to Method C, 3-quinuclidol is first reacted with a carbonyldiimidazole (DCI) in an inert solvent (e.g. DCM, 1,2-DCE) at room temperature in order to obtain the corresponding imidazole-1-carboxylic acid 1-azabicyclo[2.2.2]oct-3-yl ester. Then, arylalkylamine (II) is metalated in an inert solvent (e.g. THF) using BuLi and the ester was added at a temperature ranging from 0° C. to room temperature.

Sources & evidence

ORD record
ord-9e72c49c8a3b4228b86498fe8cd09f7b
Source dataset
uspto-grants-2008_11
Patent number
US07452904B2

Reaction notes

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