[(S)-3-(4-Fluoro-benzyl)piperidin-1-yl]-[(3S,4R)-3-((R)-1-phenyl-ethylamino)-tetrahydro-pyran-4-yl]-methanone → HCID 69748357, compound

HRID 497492Notes

Reaction equation

HRID 497492 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C@@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([C:13]([C@@H:15]3[CH2:20][CH2:19][O:18][CH2:17][C@H:16]3[NH:21][C@@H](C3C=CC=CC=3)C)=[O:14])[CH2:8]2)=[CH:4][CH:3]=1>[OH-].[Pd+2].[OH-].C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([C:13]([C@@H:15]3[CH2:20][CH2:19][O:18][CH2:17][C@H:16]3[NH2:21])=[O:14])[CH2:8]2)=[CH:30][CH:31]=1

Participants

4

Reactant 1

HCID 69748122[(S)-3-(4-Fluoro-benzyl)piperidin-1-yl]-[(3S,4R)-3-((R)-1-phenyl-ethylamino)-tetrahydro-pyran-4-yl]-methanone

Product 1

HCID 69748357HCID 69748357, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

[(S)-3-(4-Fluoro-benzyl)-piperidin-1-yl]-[(3S,4R)-3-((R)-1-phenyl-ethylamino)-tetrahydro-pyran-4-yl]-methanone (1.10 g, 2.6 mmol), palladium hydroxide (20 weight % on carbon, dry basis; 440 mg) and ethanol (40 mL) were combined in a pressure bottle and shaken under a hydrogen atmosphere (55-60 psig) for 20 h. The mixture was filtered through Celite, and the solids were washed thoroughly with ethanol. The filtrate was concentrated to give the product as a glassy foam (803 mg, 96%), used without further purification.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe solids were washed thoroughly with ethanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b57d8f37d8184fd08bea01a2536a1d6a
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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