tert-Butyl 7-benzyl-6-oxo-1,7-diazaspiro[4.5]decane-1-carboxylate → tert-Butyl 1,7-diazaspiro[4.5]decane-1-carboxylate

HRID 1912443Notes

Reaction equation

HRID 1912443 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2([CH2:17][CH2:16][CH2:15][N:14](CC3C=CC=CC=3)[C:13]2=O)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.CO.[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-]>[C:1]([O:5][C:6]([N:8]1[C:12]2([CH2:17][CH2:16][CH2:15][NH:14][CH2:13]2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 49761028tert-Butyl 7-benzyl-6-oxo-1,7-diazaspiro[4.5]decane-1-carboxylate

Product 1

HCID 24741699tert-Butyl 1,7-diazaspiro[4.5]decane-1-carboxylateYield 96.2%

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 7-benzyl-6-oxo-1,7-diazaspiro[4.5]decane-1-carboxylic acid tert-butyl ester (76 mg) in tetrahydrofuran/methanol (1 ml/1 ml) was added 20% palladium hydroxide carbon (15 mg), and the mixture was hydrogenated under 4 atmospheres. The mixture was filtered through Celite under nitrogen, and the filtrate was concentrated under reduced pressure to give the titled compound (51 mg).

Workup

  1. filtrationThe mixture was filtered through Celite under nitrogen
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c3b05239506c4abdb91763593fbf4afe
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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