HCID 67083165, compound → HCID 86654268, compound

HRID 42169Notes

Reaction equation

HRID 42169 reaction equation
[Cl:1][C:2]1[C:3]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[N:4][CH:5]=[C:6]([C:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH:13]=2)[CH:7]=1>C(OCC)(=O)C.[Pt]=O>[Cl:1][C:2]1[C:3]([CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=2)=[N:4][CH:5]=[C:6]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)[CH:7]=1

Participants

4

Reactant 1

HCID 67083165HCID 67083165, compound

Product 1

HCID 86654268HCID 86654268, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-[3-chloro-2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]-3,6-dihydro-2H-pyridine-1-carboxylate (Example 70) (50 mg, 0.104 mmol) in ethyl acetate (1 mL) was added platinum oxide (5 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=1/1) to give the title compound as a white amorphous (13 mg, yield 26%).

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-07df69f8b5f8449196c248fbb67cdb3e
Source dataset
uspto-grants-2013_09
Patent number
US08536176B2

Reaction notes

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