HCID 54454139, compound → HCID 53836357, compound

HRID 369904Notes

Reaction equation

HRID 369904 reaction equation
C(OC([NH:11][CH2:12][C:13]1([CH3:36])[CH2:18][CH2:17][N:16]([C:19](=[O:35])[C@:20]([C@@H:28]2[CH2:32][CH2:31][C:30]([F:34])([F:33])[CH2:29]2)([OH:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:15][CH2:14]1)=O)C1C=CC=CC=1>CO.[C].[Pd]>[NH2:11][CH2:12][C:13]1([CH3:36])[CH2:18][CH2:17][N:16]([C:19](=[O:35])[C@:20]([C@@H:28]2[CH2:32][CH2:31][C:30]([F:33])([F:34])[CH2:29]2)([OH:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 54454139HCID 54454139, compound

Product 1

HCID 53836357HCID 53836357, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 16 mg of 4-benzyloxycarbonylaminomethyl-1-{(2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetyl}-4-methylpiperidine in 2 ml of methanol, 4 mg of 10% palladium-carbon catalyst was added, followed by stirring,for 4 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 3N sodium hydroxide, the aqueous layer was extracted with chloroform. The organic layer was then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 3.5 mg of the title compound as a colorless oily substance.

Workup

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

Sources & evidence

ORD record
ord-f1dbd49530f04df29e6812b06abf1a7e
Source dataset
uspto-grants-2000_10
Patent number
US06140333

Reaction notes

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