Tert-Butyl 4-[2-(4-methanesulfonylbenzoylamino)-pyridin-5-yl]-3,6-dihydro-2H-pyridine-1-carboxylate → Tert-Butyl 4-[2-(4-methanesulfonylbenzoylamino)pyridin-5-yl]piperidine-1-carboxylate

HRID 42139

Reaction equation

HRID 42139 reaction equation
[CH3:1][S:2]([C:5]1[CH:32]=[CH:31][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH:23]=3)=[CH:14][N:13]=2)=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3]>CO.[C].[Pd]>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:20][CH2:19]3)=[CH:14][N:13]=2)=[O:10])=[CH:31][CH:32]=1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 67083258Tert-Butyl 4-[2-(4-methanesulfonylbenzoylamino)-pyridin-5-yl]-3,6-dihydro-2H-pyridine-1-carboxylate

Product 1

HCID 67083252Tert-Butyl 4-[2-(4-methanesulfonylbenzoylamino)pyridin-5-yl]piperidine-1-carboxylateYield 57%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-[2-(4-methanesulfonylbenzoylamino)pyridin-5-yl]-3,6-dihydro-2H-pyridine-1-carboxylate (83 mg, 0.18 mmol) in methanol (2 mL) was added 10% palladium-carbon (8.3 mg). The mixture was hydrogenated at room temperature for 4 hours and filtered through Celite pad. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/3) to give the title compound as a white crystal (47 mg, yield 57%).

Workup

  1. filtrationfiltered through Celite pad
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/3)

Sources & evidence

ORD record
ord-0d304eb99e614532af5208d05dd039ab
Source dataset
uspto-grants-2013_09
Patent number
US08536176B2

Linked notes

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