Sodium hydride → HCID 54333047, compound

HRID 1077414Notes

Reaction equation

HRID 1077414 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:17])[CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:7][CH2:8][S:9][CH3:10].[N:18]12[CH2:25]C[CH:21]([CH2:22][CH2:23]1)[C@@H:20](O)[CH2:19]2>C1(C)C=CC=CC=1>[CH3:10][S:9][CH2:8][CH2:7][CH:6]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:5]([O:4][C@@H:3]1[CH:21]2[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]2)[CH2:25]1)=[O:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 914043-Quinuclidinol, (-)-HCID 19431592HCID 19431592, compound

Product 1

HCID 54333047HCID 54333047, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Sodium hydride (0.64 g, as an 80% dispersion in oil) was added to a mixture of methyl-(RS)-4-(methylthio)-2-phenylbutanoate (see Preparation 11) (19.1 g) and (R)-3-quinuclidinol (prepared as described in Acta. Pharm. Suec., 281, 16, 1979) (12.7 g) in toluene (440 ml). The mixture was refluxed with continuous removal of distillate and when necessary replacement with fresh toluene for 1.5 hours. The cooled mixture was extracted with 2M hydrochloric acid, the aqueous layer washed with ethylacetate, basified with potassium carbonate and extracted with chloroform. The organic layer was dried over sodium sulphate, evaporated and the residue partitioned between ethylacetate and aqueous 10% potassium carbonate. The organic layer was dried over sodium sulphate and evaporated to leave the title compound (22.4 g, 82%) as a yellow oil.

Workup

  1. extractionThe cooled mixture was extracted with 2M hydrochloric acid
  2. washthe aqueous layer washed with ethylacetate
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customevaporated
  6. customthe residue partitioned between ethylacetate and aqueous 10% potassium carbonate
  7. dry with materialThe organic layer was dried over sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-df9171b532c74de58a6c4f7895d48757
Source dataset
uspto-grants-1996_08
Patent number
US05543419

Reaction notes

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