HCID 66732080, compound → HCID 66732452, compound

HRID 1963302Notes

Reaction equation

HRID 1963302 reaction equation
[CH3:1][S:2]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=2)[C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3]>C(O)(=O)C.O=[Pt]=O>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][CH:10]2[CH2:11][CH:12]([C:13]([O:15][CH3:16])=[O:14])[CH2:17][CH2:18][NH:19]2)=[CH:20][CH:21]=1)(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 66732080HCID 66732080, compound

Product 1

HCID 66732452HCID 66732452, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 2-(4-(methylsulfonyl)benzyl)isonicotinate (8.0 g, 26.2 mmol) was dissolved in acetic acid (250 mL). Activated carbon was added and stirred for 30 min. The activated carbon was filtered off. To the solution was added PtO2 (0.119 g, 0.52 mmol) and the reaction mixture hydrogenated in a Büchi hydrogenator overnight at room temperature and 9 bar. The catalyst was filtered off. The solvent was evaporated. The crude was partitioned between Na2CO3 (aq) and ethyl acetate. The organic layer was dried over Na2SO4, filtered through celite and evaporated to yield methyl 2-(4-(methylsulfonyl)benzyl)piperidine-4-carboxylate (5.38 g, 65.9%).

Workup

  1. additionActivated carbon was added
  2. filtrationThe activated carbon was filtered off
  3. customhydrogenated in a Büchi hydrogenator overnight
  4. customat room temperature
  5. filtrationThe catalyst was filtered off
  6. customThe solvent was evaporated
  7. customThe crude was partitioned between Na2CO3 (aq) and ethyl acetate
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered through celite
  10. customevaporated

Sources & evidence

ORD record
ord-a25e388b11c345aaac729b89494c207e
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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