Benzyl 3-(3-(methylsulfonamido)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate → N-(3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenyl)methanesulfonamide

HRID 1751138Notes

Reaction equation

HRID 1751138 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([CH:37]=[CH:38][CH:39]=1)[CH2:9][N:10]1[C:14](=[O:15])[C:13]2([CH2:20][CH2:19][N:18](C(OCC3C=CC=CC=3)=O)[CH2:17][CH2:16]2)[N:12]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:11]1)(=[O:4])=[O:3]>CO.[Pd]>[O:15]=[C:14]1[C:13]2([CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)[N:12]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:11][N:10]1[CH2:9][C:8]1[CH:7]=[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 1

HCID 66652309Benzyl 3-(3-(methylsulfonamido)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 66652299N-(3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenyl)methanesulfonamideYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 3-(3-(methylsulfonamido)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.82 g, 1.49 mmol) in methanol (15 mL), was added 10 wt % palladium on carbon (0.15 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 N-(3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenyl)methanesulfonamide (0.62 g, 99%).

Workup

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

Sources & evidence

ORD record
ord-95147ad5edcc4718bc5fdb23271004c3
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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