Acetic Acid → 2-(4-(Trifluoromethoxy)phenyl)-2,8-diazaspiro[4.5]decan-1-one

HRID 2194160Notes

Reaction equation

HRID 2194160 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)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)(=O)C>[OH-].[OH-].[Pd+2].CO>[F:27][C:24]([F:25])([F:26])[O:23][C:20]1[CH:21]=[CH:22][C:17]([N:14]2[CH2:13][CH2:12][C:11]3([CH2:10][CH2:9][NH:8][CH2:29][CH2:28]3)[C:15]2=[O:16])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 53233981HCID 53233981, compound

Product 1

HCID 667427592-(4-(Trifluoromethoxy)phenyl)-2,8-diazaspiro[4.5]decan-1-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 8-benzyl-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (3.14 g, 0.007 mol), acetic acid (5 ml) and Pearlman's catalyst (0.43 mg) in MeOH (40 ml) was stirred at room temperature under an atmospheric pressure of H2 for 3 h. The catalyst was removed by filtration and the filtrate was evaporated to give a crude residue which was triturated with diethyl ether (50 ml) to give 2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one; acetic acid salt as a white solid (1.43 g, 49%). MS (ESI): 315.1 (MH+).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customto give a crude residue which
  4. customwas triturated with diethyl ether (50 ml)

Sources & evidence

ORD record
ord-2ca38ce7ccd24dffae45c6e1504bd597
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

Loading…