Methanol → (S)-Methyl piperidine-2-carboxylate

HRID 409492

Reaktionsgleichung

Reaktionsgleichung von HRID 409492
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:14]O>>[CH3:14][O:8][C:7]([C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][NH:1]1)=[O:9]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 439227Pipecolic acid, (-)-

Produkt 1

HCID 853680(S)-Methyl piperidine-2-carboxylateAusbeute 56 %

Versuchsvorschrift

To a mixture of (S)-piperidine-2-carboxylic acid (10 mmol, 1.29 g) in MeOH (20 mL) is dropwise added thionyl chloride (30 mmol, 2.17 mL) at room temperature. The mixture is stirred at 2 hours, and then concentrated under reduced pressure. To the residue is added water (5 mL) and basified with potassium carbonate. The mixture is extracted with CH2Cl2. The combined organic layer is dried over Na2SO4, filtrated, and concentrated under reduced pressure to give (S)-piperidine-2-carboxylic acid methyl ester as a pale brown oil (800 mg, 56%).

Aufarbeitung

  1. customat room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue is added water (5 mL)
  4. extractionThe mixture is extracted with CH2Cl2
  5. dry with materialThe combined organic layer is dried over Na2SO4
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0cdca4ad2b6240f19189e7439f27417c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759365B2

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