Diphosgene → (3R)-1-azabicyclo[2.2.2]octan-3-yl carbonochloridate hydrochloride
Reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([OH:9])[CH2:2]2.[Cl:10][C:11](OC(Cl)(Cl)Cl)=[O:12]>C(#N)C>[ClH:10].[C:11]([Cl:10])(=[O:12])[O:9][C@@H:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of (R)-3-quinuclidinol (2.5 g, 19.66 mmol) in acetonitrile (200 mL) was added trichloromethyl chloroformate (3.06 mL, 25.57 mmol) dropwise at 0° C., and the mixture was allowed to stir at 0° C. for 1 hour. The reaction mixture was then stirred at RT for 16 hours, and then the solvent was removed in vacuo to afford the title compound as a white solid (4.39 g, 98%).
Workup
- stirringThe reaction mixture was then stirred at RT for 16 hours
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-c2394a7a21ce4e0dbc8d20d52015f76f
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169245B2
Reaction notes
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