Acetic Acid → (S)-6-Oxo-2-piperidinecarboxylic acid

HRID 2176456Notes

Reaction equation

HRID 2176456 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)[C:3]([OH:5])=[O:4].C(O)(=O)C>O>[O:11]=[C:9]1[NH:1][C@H:2]([C:3]([OH:5])=[O:4])[CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 92136L-2-Aminoadipic Acid

Product 1

HCID 11126383(S)-6-Oxo-2-piperidinecarboxylic acidYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (S)-2-amino-hexanedioic acid (50 g, 310.25 mmol), acetic acid (100 mL), and water (400 mL) water was refluxed for 3 h. The unchanged starting amino acid was filtered off (24 g) and the filtrate evaporated, dissolved in hot water (50 mL) and then cooled. A crystalline precipitate formed which was filtered to provide the title intermediate (20 g, 45% yield).

Workup

  1. temperaturewas refluxed for 3 h
  2. filtrationwas filtered off (24 g)
  3. customthe filtrate evaporated
  4. dissolutiondissolved in hot water (50 mL)
  5. temperaturecooled
  6. customA crystalline precipitate formed which
  7. filtrationwas filtered

Sources & evidence

ORD record
ord-42a6d150a8dd44c3a1c3a2e4d2ae9cc4
Source dataset
uspto-grants-2015_06
Patent number
US09066944B2

Reaction notes

Loading…