HCID 67083260, compound → HCID 44819977, compound

HRID 42143Notes

Reaction equation

HRID 42143 reaction equation
[CH3:1][S:2]([C:5]1[CH:31]=[CH:30][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH:22]=3)=[CH:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>CO.[Pt].[C]>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:19][CH2:18]3)=[CH:13][N:12]=2)=[CH:30][CH:31]=1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 67083260HCID 67083260, compound

Product 1

HCID 44819977HCID 44819977, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-[2-(4-methanesulfonylbenzyloxy)pyridin-5-yl]-3,6-dihydro-2H-pyridine-1-carboxylate (Example 6) (39 mg, 87.7 μmol) in methanol (2 mL) was added 10% platinum-carbon (15 mg). The mixture was hydrogenated at room temperature for 17 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=1/1) to give the title compound as a white crystal (20 mg, yield 51%).

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=1/1)

Sources & evidence

ORD record
ord-5d1ec4e6bacc41cf9cb8bd18451dd238
Source dataset
uspto-grants-2013_09
Patent number
US08536176B2

Reaction notes

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