Methanesulfonic Acid → HCID 11356666, compound

HRID 1241521Notes

Reaction equation

HRID 1241521 reaction equation
C(O[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2(O)[CH2:19][CH:18]([CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:17]2)=[CH:12][CH:11]=1)C1C=CC=CC=1.CS(O)(=O)=O>CCO.[Pd]>[C:10]1([CH3:9])[CH:11]=[CH:12][C:13]([CH:16]2[CH2:17][CH:18]([CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:19]2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 21934873HCID 21934873, compound2×

Product 1

HCID 11356666HCID 11356666, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirring solution of Example 212, (1-(4-benzyloxymethyl-phenyl)-3-pyrrolidin-1-ylmethyl-cyclobutanol) (200 mg, 0.57 mmol) in EtOH (10 mL) was added methane sulfonic acid (370 uL, 5.7 mmol), followed by 10% Pd/C (200 mg). The reaction vessel was purged with N2, and then pressurized with 45 psi H2. After 30 minute the reaction vessel was purged with nitrogen. The reaction was filtered through a plug of Celite and then concentrated under reduced pressure. The residual was dissolved in EtOAc and a solution of HCl (2 N in ether) was added. The solution was decanted and the residual was purified. Purification of this material was accomplished by dry pack flash column chromatograpy using a 40 g ISCO column, eluting with a gradient of 5%–15% MeOH/CH2Cl2 with 0.2% NH4OH. The product containing fractions were collected and concentrated to give the title compound (100 mg, 77% yield) as a colorless oil. The HCl salt of the title compound was made by dissolving the title compound in ethyl acetate and then adding a solution of HCl (2N in ether), the resulting colorless solid was collected and dried under reduced pressure.

Workup

  1. customThe reaction vessel was purged with N2
  2. customAfter 30 minute the reaction vessel was purged with nitrogen
  3. filtrationThe reaction was filtered through a plug of Celite
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residual was dissolved in EtOAc
  6. additiona solution of HCl (2 N in ether) was added
  7. customThe solution was decanted
  8. customthe residual was purified
  9. customPurification of this material
  10. customby dry pack flash column chromatograpy
  11. washeluting with a gradient of 5%–15% MeOH/CH2Cl2 with 0.2% NH4OH
  12. additionThe product containing fractions
  13. customwere collected
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-1a6a9cf7238642abb71273fd33e35cac
Source dataset
uspto-grants-2006_10
Patent number
US07115600B2

Reaction notes

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