Acetic Acid → HCID 58056623, compound

HRID 1260483Notes

Reaction equation

HRID 1260483 reaction equation
C([N:8]1[CH2:29][CH2:28][C:11]2([C:15](=[O:16])[N:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)[CH:10]([OH:30])[CH2:9]1)C1C=CC=CC=1.C(O)(=O)C.[OH-].[Na+]>[OH-].[OH-].[Pd+2].CO.O>[OH:30][CH:10]1[CH2:9][NH:8][CH2:29][CH2:28][C:11]21[C:15](=[O:16])[N:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:25])[F:26])=[CH:19][CH:18]=1)[CH2:13][CH2:12]2

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 56602659(5SR,6RS)-8-benzyl-6-hydroxy-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

Product 1

HCID 58056623HCID 58056623, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of (5SR,6RS)-8-benzyl-6-hydroxy-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (293 mg, 0.70 mmol), acetic acid (1 ml) and Pearlman's catalyst (195 mg) in MeOH (20 ml) was stirred at room temperature under an atmospheric pressure of H2 for 4 h. The catalyst was removed by filtration and the filtrate was evaporated to give a crude residue was dissolved in water and the solution was made basic with 1N NaOH and extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4), filtered and evaporated under reduced pressure to yield (5SR,6RS)-6-hydroxy-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one as an off white solid. MS (ESI): 331.2 (MH+).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customto give a crude residue
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a876c23056dd436b9de09871ec995704
Source dataset
uspto-grants-2013_06
Patent number
US08470843B2

Reaction notes

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