HCID 66849884, compound → AC1Ofb5V

HRID 1914584Notes

Reaction equation

HRID 1914584 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[N:13]([C@@H](C3C=CC=CC=3)CO)[C:12](=O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>[Pd].C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:9][CH2:10][CH2:11][CH2:12][NH:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 66849884HCID 66849884, compound

Product 1

HCID 7048023AC1Ofb5VYield 92.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(R)-6-(4-Fluoro-phenyl)-1-((S)-2-hydroxy-1-phenyl-ethyl)-piperidin-2-one (650 mg, 1.94 mmol) and palladium on charcoal (0.2 g) in ethanol (25 mL) were stirred under an atmosphere of hydrogen for 20 hours. The reaction mixture was filtered through Celite® then evaporated and the material dissolved in methanol and purified on a 10 g SCX-2 cartridge, eluting with 2 N ammonium hydroxide in methanol. The ammoniacal fractions were evaporated to yield the title compound (0.321 g), which was used in the synthesis of EE-46. LCMS m/z 180.11 [M+H]+ R.T.=1.3-1.6 min (Analytical Method 6).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. customthen evaporated
  3. dissolutionthe material dissolved in methanol
  4. custompurified on a 10 g SCX-2 cartridge
  5. washeluting with 2 N ammonium hydroxide in methanol
  6. customThe ammoniacal fractions were evaporated

Sources & evidence

ORD record
ord-c3b84ad64711444383b8c35f48f083e0
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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