Diphosgene → (3R)-1-azabicyclo[2.2.2]octan-3-yl carbonochloridate hydrochloride

HRID 332645Notes

Reaction equation

HRID 332645 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]1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 914043-Quinuclidinol, (-)-

Product 1

HCID 86676896(3R)-1-azabicyclo[2.2.2]octan-3-yl carbonochloridate hydrochlorideYield 151.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (R)-3-quinuclidinol (2.5 g, 19.66 mmol) in acetonitrile (200 mL), trichloromethyl chloroformate (3.06 mL, 25.57 mmol) was added dropwise at 0° C. and stirred for 1 hour. The reaction mixture was stirred at RT for 16 hours before concentrating in vacuo to afford the title compound (4.39 g, 98%).

Workup

  1. stirringThe reaction mixture was stirred at RT for 16 hours
  2. concentrationbefore concentrating in vacuo

Sources & evidence

ORD record
ord-4919b6f73e27444993f511c6bba78e52
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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