Potassium tert-butoxide → HCID 57157855, compound

HRID 975634Notes

Reaction equation

HRID 975634 reaction equation
CC(C)([O-])C.[K+].[C:7]([OH:10])(=[S:9])[CH3:8].[CH2:11]([O:14][C:15]([N:17]1[CH2:21][C@H:20](OS(C)(=O)=O)[CH2:19][C@H:18]1[CH2:27][CH2:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)=[O:16])[CH:12]=[CH2:13]>CN(C)C=O>[C:7]([S:9][C@@H:20]1[CH2:21][N:17]([C:15]([O:14][CH2:11][CH:12]=[CH2:13])=[O:16])[C@H:18]([CH2:27][CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[CH2:19]1)(=[O:10])[CH3:8]

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 54497900HCID 54497900, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 57157855HCID 57157855, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of potassium t-butoxide (1.50 g) in N,N-dimethylformamide (20 ml) was added dropwise thioacetic acid (0.96 ml) with stirring at -10°~-5° C. The mixture was stirred at the same temperature for 10 minutes. A solution of (2R,4R)-1-allyloxycarbonyl-4-methanesulfonyloxy-2-[2-(pyridin-3-yl)ethyl]pyrrolidine (3.39 g) in N,N-dimethylformamide (20 ml) was added to the mixture obtained above with stirring at the same temperature. The mixture was stirred at 80°-90° C. for 3 hours. The reaction mixture was poured into ice-water (120 ml) and extracted three times with ethyl acetate (80 ml). The extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (150 g) eluting with a mixture of chloroform and methanol (19:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2R,4S)-4-acetylthio-1-allyloxycarbonyl-2-[2-(pyridin-3-yl)ethyl]pyrrolidine (3.12 g).

Workup

  1. stirringThe mixture was stirred at the same temperature for 10 minutes
  2. customobtained above
  3. stirringwith stirring at the same temperature
  4. stirringThe mixture was stirred at 80°-90° C. for 3 hours
  5. extractionextracted three times with ethyl acetate (80 ml)
  6. washThe extract was washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated in vacuo
  9. customThe resulting residue was chromatographed on silica gel (150 g)
  10. washeluting with a mixture of chloroform and methanol (19:1, V/V)
  11. additionThe fractions containing the desired compound
  12. customwere collected
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-48a5bb8b774e4db498041a8a5dc21fe5
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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