HCID 69076131, compound → HCID 69078753, compound

HRID 1761189Notes

Reaction equation

HRID 1761189 reaction equation
[F:1][C:2]1([F:36])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:35])([C:24]2[CH:29]=[CH:28][C:27]([CH2:30]OC(=O)C)=[CH:26][CH:25]=2)[C:8]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[O:9])[CH2:3]1>CO.[OH-].[Pd+2].[OH-].[C].[H][H]>[F:36][C:2]1([F:1])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:35])([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:8]([O:10][CH:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]2)=[O:9])[CH2:3]1

Participants

5

Reactant 1

HCID 69076131HCID 69076131, compound

Product 1

HCID 69078753HCID 69078753, compoundYield 99.4%

Reagents, catalysts & solvents 3

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

To a solution of 42 mg of t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-((acetyloxy)methyl)phenyl)-ethanoyloxy)tetrahydropyridine-1(2H)-carboxylate in 1 ml of methanol, 20 mg of palladium hydroxide-carbon catalyst was added, followed by 16 hours' stirring at ambient temperature and pressure in hydrogen atmosphere. The reaction liquid was filtered with Celite and the solvent was distilled off under reduced pressure to provide 37 mg of the title compound.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered with Celite
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fed3f745ef244702a33e6215874fbdce
Source dataset
uspto-grants-2005_01
Patent number
US06846835B2

Reaction notes

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