Thionyl Chloride → methyl (2S)-piperidine-2-carboxylate hydrochloride

HRID 397657Notes

Reaction equation

HRID 397657 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C@@H]([C@H](C(O)=O)O)O)(O)=O.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[C:21]([OH:23])=[O:22]>CO>[ClH:3].[CH3:5][O:22][C:21]([C@@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20][NH:15]1)=[O:23]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 69946027(2S)-2-Piperidinecarboxylic acid L-tartrate

Product 1

HCID 13246232methyl (2S)-piperidine-2-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thionyl chloride (161 ml) was added dropwise to a suspension of (2S)-2-piperidinecarboxylic acid L-tartrate (60 g) [see Preparation 1] in methanol (800 ml) at 0° C. The reaction mixture was stirred for 18 hours at room temperature after which time the solvent was removed under reduced pressure and the product azeotroped with toluene, precipitated out using methanol and filtered to afford (2S)-2-(methoxycarbonyl)piperidine hydrochloride (37.7 g) as a white solid.

Workup

  1. customwas removed under reduced pressure
  2. customthe product azeotroped with toluene
  3. customprecipitated out
  4. filtrationfiltered

Sources & evidence

ORD record
ord-778ae1da2ae74976806c95bbe1013773
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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