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

HRID 2176461Notes

Reaction equation

HRID 2176461 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-df1efb5021fd4121b0cb742f670bd3f1
Source dataset
uspto-grants-2015_06
Patent number
US09066944B2

Reaction notes

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