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

HRID 1751060Notes

Reaction equation

HRID 1751060 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]([CH:40]=[CH:41][CH:42]=1)[CH2:11][N:12]1[C:16](=[O:17])[C:15]2([CH2:22][CH2:21][N:20](C(OCC3C=CC=CC=3)=O)[CH2:19][CH2:18]2)[N:14]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[F:39][C:36]1[CH:35]=[CH:34][C:33]([N:14]2[C:15]3([CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)[C:16](=[O:17])[N:12]([CH2:11][C:10]3[CH:9]=[C:8]([CH:42]=[CH:41][CH:40]=3)[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13]2)=[CH:38][CH:37]=1

Participants

4

Reactant 1

HCID 58046684Benzyl 3-(3-(tert-butoxycarbonyl)benzyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 66652535Tert-butyl 3-((1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 3-(3-(tert-butoxycarbonyl)benzyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.82 g, 1.43 mmol) in methanol (10 mL), was added 10 wt % palladium on carbon (0.2 g). After stirring under hydrogen at room temperature and atmospheric pressure for 4 hours, the reaction mixture was filtered, washed with methanol, concentrated in vacuo to obtain tert-butyl 3-((1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.62 g, 99%).

Workup

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

Sources & evidence

ORD record
ord-138ea0b3ffee4bdc980818848ebc2042
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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