3-Quinuclidinol, (-)- → HCID 53767445, compound

HRID 486482Notes

Reaction equation

HRID 486482 reaction equation
[C:1]1([CH2:7][C:8]([O:10][C:11](=[O:19])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=O)[CH:6]=CC=CC=1.[N:20]12CCC(C[CH2:25]1)[C@@H:22](O)[CH2:21]2>C(OCC)(=O)C>[C:13]1([CH2:12][C:11]([O:10][C@@H:8]2[CH:7]3[CH2:1][CH2:6][N:20]([CH2:21][CH2:22]3)[CH2:25]2)=[O:19])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 914043-Quinuclidinol, (-)-HCID 316205phenylacetic anhydride

Product 1

HCID 53767445HCID 53767445, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Phenylacetic acid anhydride (prepared as described in J. Org. Chem., 1588, 30, 1965) (15 g) was added to a suspension of (R)-3-quinuclidinol (5 g) in ethyl acetate (250 ml) at room temperature. After 178 hour the solvent was evaporated and the residue dissolved in hydrochloric acid (2M). This was washed with ethyl acetate, basified with sodium carbonate and extracted with ethyl acetate. The organic extract was dried over sodium sulphate and evaporated to give the title compound as a yellow oil (9 g, 66%).

Workup

  1. customAfter 178 hour the solvent was evaporated
  2. dissolutionthe residue dissolved in hydrochloric acid (2M)
  3. washThis was washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. dry with materialwas dried over sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-f4cdc91e3d5149b9b2bd69366e8a6f3d
Source dataset
uspto-grants-1994_03
Patent number
US05292749

Reaction notes

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