Sodium hydride → HCID 54167690, compound

HRID 1934384Notes

Reaction equation

HRID 1934384 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH3:9][O:10][C:11](=[O:27])/[CH:12]=[CH:13]/[CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.[Cl-].[NH4+]>CS(C)=O>[CH3:9][O:10][C:11]([C@@H:12]1[CH2:2][C@H:13]1[CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]1)=[O:27]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 10516122HCID 10516122, compound

Product 1

HCID 54167690HCID 54167690, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of trimethylsulfoxonium iodide (1.16 g, 5.25 mmol) in dimethylsulfoxide (10 ml) was added sodium hydride (60% dispersion in oil, 210 mg, 5.25 mmol) under 0° C., and the solution was stirred at room temperature for 10 minutes. To the resulting mixture was added a solution of 3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acrylic acid methyl ester (1.37 g, 5.09 mmol) was added dropwise under 0° C., and it was stirred for 1 hour at room temperature and for 2 hours at 50° C. After cooling to 0° C., saturated aqueous ammonium chloride was added to quench the reaction. The mixture was extracted with diethyl ether 50 ml×2), and the organic phase was washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by column chromatography (n-hexane/ethyl acetate=7/1) to give 2-(1-tert-butoxycarbonyl-4-piperidyl)-(1R*,2S*)-cyclopropane-1-carboxylic acid methyl ester.

Workup

  1. additionwas added dropwise under 0° C.
  2. stirringit was stirred for 1 hour at room temperature and for 2 hours at 50° C
  3. temperatureAfter cooling to 0° C.
  4. customto quench
  5. customthe reaction
  6. extractionThe mixture was extracted with diethyl ether 50 ml×2), and the organic phase
  7. washwas washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe residue was purified by column chromatography (n-hexane/ethyl acetate=7/1)

Sources & evidence

ORD record
ord-5236139c69554dc7ad4d66a39b79b72e
Source dataset
uspto-grants-2002_05
Patent number
US06384028B1

Reaction notes

Loading…