Ethanol → (S)-ethyl-6-oxopiperidine-2-carboxylate

HRID 705713Notes

Reaction equation

HRID 705713 reaction equation
S(Cl)(Cl)=O.[O:5]=[C:6]1[NH:11][C@H:10]([C:12]([OH:14])=[O:13])[CH2:9][CH2:8][CH2:7]1.[CH2:15](O)[CH3:16]>>[CH2:15]([O:13][C:12]([C@@H:10]1[CH2:9][CH2:8][CH2:7][C:6](=[O:5])[NH:11]1)=[O:14])[CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 11126383(S)-6-Oxo-2-piperidinecarboxylic acid

Product 1

HCID 13696119(S)-ethyl-6-oxopiperidine-2-carboxylate

Procedure

Absolute ethanol (300 mL) was cooled at −5° C. then thionyl chloride (14.01 mL, 192.1 mmol) was added keeping the temperature below 0° C., followed by portionwise addiction of (S)-6-oxopiperidine-2-carboxylic acid (25.0 g, 174.6 mmol). The mixture was stirred at room temperature for 6 hours. The solvent was evaporated, then toluene (300 mL) and Et3N (48.7 mL) were added. After 0.5 hour the precipitate was filtered and washed with toluene and Et2O. The filtrate was evaporated and the residue treated with Et2O. The precipitate was eliminated and the solution was concentrated to give the title compound as yellow oil. Yield (29.9 g, 100%).

Workup

  1. customthe temperature below 0° C.
  2. customThe solvent was evaporated
  3. additiontoluene (300 mL) and Et3N (48.7 mL) were added
  4. filtrationAfter 0.5 hour the precipitate was filtered
  5. washwashed with toluene and Et2O
  6. customThe filtrate was evaporated
  7. additionthe residue treated with Et2O
  8. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-a7f856fd20994da2bafc65167aa89caf
Source dataset
uspto-grants-2015_11
Patent number
US09174977B2

Reaction notes

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