Methanol → 2-Piperidinecarboxylic acid, 6-oxo-, methyl ester, (2S)-

HRID 2203140Notes

Reaction equation

HRID 2203140 reaction equation
[O:1]=[C:2]1[NH:7][C@H:6]([C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3]1.S(Cl)(Cl)=O.[CH3:15]O>>[O:1]=[C:2]1[NH:7][C@H:6]([C:8]([O:10][CH3:15])=[O:9])[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 11126383(S)-6-Oxo-2-piperidinecarboxylic acid

Product 1

HCID 111265192-Piperidinecarboxylic acid, 6-oxo-, methyl ester, (2S)-

Procedure

To a solution of (S)-6-oxopiperidine-2-carboxylic acid (17 g, 120 mmol) in methanol (200 mL) was added thionyl chloride (87 mL, 1.2 mol) and the reaction mixture was stirred at RT overnight, concentrated, combined with the product of a similar preparation, washed with saturated aqueous NaHCO3, and extracted with EtOAc (4×200 mL). The organic layers were combined, dried over sodium sulfate and evaporated to provide crude (S)-methyl 6-oxopiperidine-2-carboxylate (36.5 g).

Workup

  1. concentrationconcentrated
  2. customcombined with the product of a similar preparation
  3. washwashed with saturated aqueous NaHCO3
  4. extractionextracted with EtOAc (4×200 mL)
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-3b9136e8cdd2473a96dcf3a886a92f3b
Source dataset
uspto-grants-2016_06
Patent number
US09365549B2

Reaction notes

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