Methanesulfonic Acid → HCID 20589484, compound

HRID 413680Notes

Reaction equation

HRID 413680 reaction equation
[OH:1][CH:2]([C:14]1(O)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17][C:16]2[CH:25]=[CH:26][CH:27]=[CH:28][C:15]1=2)[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([C:11]([OH:13])=[O:12])[CH2:6]1.CS(O)(=O)=O>ClCCl>[CH:25]1[C:16]2[CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH:14]([C:2](=[O:1])[CH2:3][CH2:4][N:5]3[CH2:10][CH2:9][CH2:8][C@@H:7]([C:11]([OH:13])=[O:12])[CH2:6]3)[C:15]=2[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 70010731HCID 70010731, compound

Product 1

HCID 20589484HCID 20589484, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above 3-piperidinecarboxylic acid (2.84 g, 5.3 mmol) was dissolved in dichloromethane (200 ml), methanesulfonic acid (0.5 ml) was added and the resulting mixture was heated at reflux temperature for 2 days. The mixture was allowed to cool and was then concentrated in vacuo. The residue was dissolved in water (50 ml) and extracted with dichloromethane (4×50 ml). The combined organic extracts were concentrated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol (9:1) as eluent. This afforded after evaporation of the solvent 0.74 g of the title compound.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux temperature for 2 days
  3. temperatureto cool
  4. concentrationwas then concentrated in vacuo
  5. dissolutionThe residue was dissolved in water (50 ml)
  6. extractionextracted with dichloromethane (4×50 ml)
  7. concentrationThe combined organic extracts were concentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel using
  9. additiona mixture of dichloromethane and methanol (9:1) as eluent
  10. customThis afforded
  11. customafter evaporation of the solvent 0.74 g of the title compound

Sources & evidence

ORD record
ord-4d908d5469f043d68939b291ab8bb870
Source dataset
uspto-grants-2003_05
Patent number
US06569849B1

Reaction notes

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