Benzyl 3-(4-(1-tert-butoxy-2-methyl-1-oxopropan-2-yloxy)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate → Tert-butyl 2-methyl-2-(4-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenoxy)propanoate

HRID 1751049Notes

Reaction equation

HRID 1751049 reaction equation
[C:1]([O:5][C:6](=[O:45])[C:7]([CH3:44])([O:9][C:10]1[CH:43]=[CH:42][C:13]([CH2:14][N:15]2[C:19](=[O:20])[C:18]3([CH2:25][CH2:24][N:23](C(OCC4C=CC=CC=4)=O)[CH2:22][CH2:21]3)[N:17]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:16]2)=[CH:12][CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C.CO>[CH3:44][C:7]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][N:15]2[C:19](=[O:20])[C:18]3([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[N:17]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:16]2)=[CH:42][CH:43]=1)([CH3:8])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:45]

Participants

4

Reactant 1

HCID 58046766Benzyl 3-(4-(1-tert-butoxy-2-methyl-1-oxopropan-2-yloxy)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 66652186Tert-butyl 2-methyl-2-(4-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenoxy)propanoateYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of benzyl 3-(4-(1-tert-butoxy-2-methyl-1-oxopropan-2-yloxy)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.69 g, 1.12 mmol) in 1:1 solution of ethyl acetate/methanol (20 mL), was added 10 wt % palladium on carbon (0.2 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-methyl-2-(4-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenoxy)propanoate (0.5 g, 93%).

Workup

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

Sources & evidence

ORD record
ord-a70c0151bf1649f3ab03052613e19d57
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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