Sodium Hydroxide → (2RS,5RS)-1-methanesulfonyl-piperidine-2,5-dicarboxylic acid 2-methyl ester

HRID 1006846Notes

Reaction equation

HRID 1006846 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([O:13]C)=[O:12])[CH2:7][N:6]1[S:15]([CH3:18])(=[O:17])=[O:16])=[O:4].[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([OH:13])=[O:12])[CH2:7][N:6]1[S:15]([CH3:18])(=[O:17])=[O:16])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69427827HCID 69427827, compound

Product 1

HCID 69433575(2RS,5RS)-1-methanesulfonyl-piperidine-2,5-dicarboxylic acid 2-methyl esterYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (2RS,5RS)-1-methanesulfonyl-piperidine-2,5-dicarboxylic acid dimethyl ester (46.5 g) in methanol (850 ml) and water (85 ml) was added 1 molar sodium hydroxide (166 ml) within 20 minutes at reflux temperature. The reaction mixture was stirred for 45 minutes at reflux, cooled and concentrated. The residue was taken up in water (300 ml) and washed with Et2O. The aqueous phase was acidified with 1 molar HCl (166 ml) and extracted with EtOAc. The organic phase was washed with brine, dried over magnesium sulphate and concentrated. The residue was crystallized from acetone/Et2O to obtain (2RS,5RS)-1-methanesulfonyl-piperidine-2,5-dicarboxylic acid 2-methyl ester (16.8 g) as a colourless solid, mp 130-133° C., MS: 206 (M+-59).

Workup

  1. temperatureat reflux temperature
  2. temperatureat reflux
  3. temperaturecooled
  4. concentrationconcentrated
  5. washwashed with Et2O
  6. extractionextracted with EtOAc
  7. washThe organic phase was washed with brine
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated
  10. customThe residue was crystallized from acetone/Et2O

Sources & evidence

ORD record
ord-1edfb39b35af41a58d58f38a87f76bac
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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