Diphosgene → (3R)-1-azabicyclo[2.2.2]octan-3-yl carbonochloridate hydrochloride
Reaction equation
[Cl:1][C:2]([O:4][C:5](Cl)(Cl)Cl)=[O:3].[N:9]12[CH2:16]C[CH:12]([CH2:13][CH2:14]1)[C@@H:11](O)[CH2:10]2>ClCCl>[ClH:1].[Cl:1][C:2]([O:4][C@@H:5]1[CH:12]2[CH2:13][CH2:14][N:9]([CH2:10][CH2:11]2)[CH2:16]1)=[O:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 8.7 mL (74.8 mmol) of trichloromethyl chloroformate in 240 mL of dichloromethane, a solution of 4.75 g (37.4 mmol) of (R)-3-quinuclidol in 240 mL of dichloromethane was added dropwise at 0° C. in inert atmosphere and with continuous stirring. Then, the mixture was stirred at room temperature for 24 h, and the solvent was distilled off under reduced pressure to give 8.46 g (37.4 mmol) of a white solid corresponding to the title compound. IR (KBr, cm−1): 3380, 2650–2500, 1776.
Workup
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-4b37777a4c1446a88ceaed617dcc410d
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115629B2
Reaction notes
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