HCID 54251644, compound → HCID 44308746, compound

HRID 369903Notes

Reaction equation

HRID 369903 reaction equation
C(OC([NH:11][C:12]1([CH3:35])[CH2:17][CH2:16][N:15]([C:18](=[O:34])[C@:19]([C@@H:27]2[CH2:31][CH2:30][C:29]([F:33])([F:32])[CH2:28]2)([OH:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][CH2:13]1)=O)C1C=CC=CC=1>CO.C(OCC)(=O)C.[C].[Pd]>[NH2:11][C:12]1([CH3:35])[CH2:17][CH2:16][N:15]([C:18](=[O:34])[C@:19]([C@@H:27]2[CH2:31][CH2:30][C:29]([F:32])([F:33])[CH2:28]2)([OH:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 1

HCID 54251644HCID 54251644, compound

Product 1

HCID 44308746HCID 44308746, compoundYield 77.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 568 mg of 4-benzyloxycarbonylamino-1-{(2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetyl}-4-methylpiperidine in a mixture of 10 ml of methanol and 5 ml of ethyl acetate, 200 mg of 10% palladium-carbon catalyst was added, followed by stirring for 18 hours under a hydrogen atmosphere. After filtering the catalyst off, the solvent was distilled off under reduced pressure, and the resulting residue was dissolved in 1M hydrochloric acid and washed with diethyl ether. After basifying with 4N sodium hydroxide, the aqueous layer was extracted with chloroform, and dried over anhydrous magnesium sulfate to give 320 mg of the title compound as a colorless oily substance.

Workup

  1. additionwas added
  2. filtrationAfter filtering the catalyst off, the solvent
  3. distillationwas distilled off under reduced pressure
  4. dissolutionthe resulting residue was dissolved in 1M hydrochloric acid
  5. washwashed with diethyl ether
  6. extractionthe aqueous layer was extracted with chloroform
  7. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-02fc5c373422441e84188ff756439113
Source dataset
uspto-grants-2000_10
Patent number
US06140333

Reaction notes

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