3-Quinuclidinol, (-)- → HCID 86627861, compound

HRID 660069Notes

Reaction equation

HRID 660069 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([OH:9])[CH2:2]2.[Br:10][CH:11]([CH3:20])[C:12]([NH:14][C:15]1[CH:19]=[CH:18][O:17][N:16]=1)=[O:13]>C(Cl)(Cl)Cl.C(#N)C>[Br-:10].[OH:9][C@@H:3]1[CH:4]2[CH2:7][CH2:8][N+:1]([CH:11]([C:12](=[O:13])[NH:14][C:15]3[CH:19]=[CH:18][O:17][N:16]=3)[CH3:20])([CH2:6][CH2:5]2)[CH2:2]1

Participants

4

Reactant 2

HCID 914043-Quinuclidinol, (-)-HCID 67537435HCID 67537435, compound

Product 1

HCID 86627861HCID 86627861, compound

Reagents, catalysts & solvents 1

HCID 22555007Acetonitrile chloroformSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of (R)-1-aza-bicyclo[2.2.2]octan-3-ol (0.267 g, 2.1 mmol) in chloroform/acetonitrile (1:1) (4 ml) is added 2-bromo-N-isoxazol-3-yl-propionamide [G(i)](0.5 g, 2.28 mmol) and the reaction mixture heated in a microwave at 90° C. for 3 hours. Purification using C-18 reverse phase column chromatography (eluent: water-acetonitrile) yields the titled compound.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-bae7a6644a704b1ca97bdfb62ad1209b
Source dataset
uspto-grants-2011_12
Patent number
US08084463B2

Reaction notes

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