Water → imidazole-1-carboxylic acid (R)-1-aza-bicyclo[2.2.2]oct-3-yl ester

HRID 1951613Notes

Reaction equation

HRID 1951613 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H: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].O>C(Cl)Cl>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H: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 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 914043-Quinuclidinol, (-)-

Product 1

HCID 59187189imidazole-1-carboxylic acid (R)-1-aza-bicyclo[2.2.2]oct-3-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, 7.0 g (55.0 mmol) of (R)-3-quinuclidinol were suspended in 100 ml of CH2Cl2. After cooling the suspension to 0° C., a solution of 1,1′-carbonyldiimidazole (10.7 g, 66.0 mmol) in 150 mL of CH2Cl2 was added. The reaction mixture was stirred at 0° C. for 4 hours, then water was added (100 ml). The organic layer was separated, washed with water, dried over sodium sulphate and the solvent was evaporated under reduced pressure. The residue oil (13.1 g) was used without further purification.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over sodium sulphate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue oil (13.1 g) was used without further purification

Sources & evidence

ORD record
ord-59f27db1c1e34d05b545d1050208b572
Source dataset
uspto-grants-2013_03
Patent number
US08404712B2

Reaction notes

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