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

HRID 409492

Reaction equation

HRID 409492 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-0cdca4ad2b6240f19189e7439f27417c
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Linked notes

Loading…