Methanol → (S)-Methyl piperidine-2-carboxylate
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
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
- customat room temperature
- concentrationconcentrated under reduced pressure
- additionTo the residue is added water (5 mL)
- extractionThe mixture is extracted with CH2Cl2
- dry with materialThe combined organic layer is dried over Na2SO4
- filtrationfiltrated
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-0cdca4ad2b6240f19189e7439f27417c
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759365B2
Reaction notes
Loading…