Benzyl 3-(2-(tert-butoxycarbonyl)benzyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate → Tert-butyl 2-((1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

HRID 1751080Notes

Reaction equation

HRID 1751080 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:42]=[CH:41][CH:40]=[CH:39][C:9]=1[CH2:10][N:11]1[C:15](=[O:16])[C:14]2([CH2:21][CH2:20][N:19](C(OCC3C=CC=CC=3)=O)[CH2:18][CH2:17]2)[N:13]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[F:38][C:35]1[CH:36]=[CH:37][C:32]([N:13]2[C:14]3([CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[C:15](=[O:16])[N:11]([CH2:10][C:9]3[CH:39]=[CH:40][CH:41]=[CH:42][C:8]=3[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:12]2)=[CH:33][CH:34]=1

Participants

4

Reactant 1

HCID 58046690Benzyl 3-(2-(tert-butoxycarbonyl)benzyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 66652103Tert-butyl 2-((1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 3-(2-(tert-butoxycarbonyl)benzyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate (1.5 g, 2.61 mmol) in methanol (25 mL), was added 10 wt % palladium on carbon (0.25 g). After stirring under hydrogen at room temperature and atmospheric pressure for 2 hours, the reaction mixture was filtered, washed with methanol, concentrated in vacuo to obtain tert-butyl 2-((1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (1.1 g, 96%).

Workup

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

Sources & evidence

ORD record
ord-7ca7c41ff3db4da1ac885dd8853e59f9
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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