HCID 117840323, compound → HCID 117840875, compound

HRID 714864Notes

Reaction equation

HRID 714864 reaction equation
[CH3:1][NH:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4]>C(O)C.[C].[Pd]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:5]2([C:3]([NH:2][CH3:1])=[O:4])[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 117840323HCID 117840323, compound

Product 1

HCID 117840875HCID 117840875, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-methyl-4-(4-nitrophenyl)tetrahydro-2H-pyran-4-carboxamide (380 mg) obtained in Step C of Example 151 in ethanol (20 mL) was added 10% palladium-carbon (100 mg), and the mixture was stirred at room temperature for 10 hr under hydrogen atmosphere (at normal pressures). The palladium-carbon was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (330 mg).

Workup

  1. customThe palladium-carbon was removed by filtration through Celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e7d124c19ef34e47933002463d0fadbe
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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