Acetic Acid → HCID 28280528, compound

HRID 1976239Notes

Reaction equation

HRID 1976239 reaction equation
Cl.[S:2]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1CC#N)([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:20]([OH:23])(=[O:22])[CH3:21]>>[S:2]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[CH2:21][C:20]([OH:23])=[O:22])([C:5]1[CH:6]=[CH:7][C:8]([CH3:9])=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 57059856HCID 57059856, compound

Product 1

HCID 28280528HCID 28280528, compoundYield 48.2%

Procedure

Concentrated hydrochloric acid (20 ml) was added to a solution of (2S)-2-(1-tosylpyrrolidin-2-yl) acetonitrile (4.35 g) prepared in Reference Example 50 in acetic acid (4 ml) and then the reaction solution was heated under reflux for 3 hours. After cooling the reaction solution, it was poured into ice water and then extracted with ether. The resulting organic phase was washed with water, dried over anhydrous magnesium sulfate and then concentrated. The resulting residue was subjected to silica gel column chromatography and then eluted with chloroform/methanol (99/1) to give 6.93 g (yield 48.2%) of the title compound.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling the reaction solution, it
  4. extractionextracted with ether
  5. washThe resulting organic phase was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. washeluted with chloroform/methanol (99/1)

Sources & evidence

ORD record
ord-4e941b5b620e42929a1b9c54485967e6
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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