3-Quinuclidinol, (-)- → HCID 53856390, compound

HRID 486484Notes

Reaction equation

HRID 486484 reaction equation
[C:1]1([CH:7]([CH2:12][CH2:13][N:14]2[CH:18]=[CH:17][CH:16]=[N:15]2)[C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:19]12[CH2:26]C[CH:22]([CH2:23][CH2:24]1)[C@@H:21](O)[CH2:20]2>C1(C)C=CC=CC=1>[C:1]1([CH:7]([CH2:12][CH2:13][N:14]2[CH:18]=[CH:17][CH:16]=[N:15]2)[C:8]([O:10][C@@H:11]2[CH:22]3[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]3)[CH2:26]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 914043-Quinuclidinol, (-)-HCID 53893447HCID 53893447, compound

Product 1

HCID 53856390HCID 53856390, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of methyl (RS)-2-phenyl-4-(1H-pyrazol-1-yl)butanoate (see Preparation 17) (0.37 g), (R)-3-quinuclidinol (0.24 g) sodium hydride (15 mg, as an 80% dispersion in oil) in toluene (15 ml) as refluxed with continuous removal of distillate and, when necessary, replacement with fresh toluene, for 11/2 hours. The cooled mixture was successively washed with water then saturated brine and extracted with 2M hydrochloric acid. The aqueous layer was washed with ethyl acetate, basified with potassium carbonate and extracted with ethyl acetate. The organic layer was dried over magnesium sulphate and evaporated to give the title compound (0.31 g, 61%) as a yellow oil

Workup

  1. custom2 hours
  2. washThe cooled mixture was successively washed with water
  3. extractionsaturated brine and extracted with 2M hydrochloric acid
  4. washThe aqueous layer was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-50032996949e4cd58f49978822fcd0e2
Source dataset
uspto-grants-1994_03
Patent number
US05292749

Reaction notes

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