Benzyl 3-(3-(methoxycarbonyl)phenyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate → Methyl 3-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoate

HRID 2363055Notes

Reaction equation

HRID 2363055 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([N:11]2[C:15](=[O:16])[C:14]3([CH2:21][CH2:20][N:19](C(OCC4C=CC=CC=4)=O)[CH2:18][CH2:17]3)[N:13]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:12]2)[CH:8]=[CH:9][CH:10]=1)=[O:4]>CO.[Pd]>[O:16]=[C:15]1[C:14]2([CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2)[N:13]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:12][N:11]1[C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

4

Reactant 1

HCID 66652870Benzyl 3-(3-(methoxycarbonyl)phenyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 66652446Methyl 3-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoateYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 3-(3-(methoxycarbonyl)phenyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.18 g, 0.36 mmol) in methanol (4 mL), was added 10 wt % palladium on carbon (0.036 g). After stirring under hydrogen at room temperature and atmospheric pressure for 18 hours, the reaction mixture was filtered, washed with methanol, concentrated in vacuo to obtain methyl 3-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoate (0.12 g).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washwashed with methanol
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd222bdee69d47d0bb6d3f0d0aa8e723
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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