6-Benzyl-8,8-dimethyl-6,9-diaza-spiro[4.5]decane-9-carboxylic acid tert-butyl ester → tert-Butyl 8,8-dimethyl-6,9-diazaspiro[4.5]decane-9-carboxylate

HRID 2360714Notes

Reaction equation

HRID 2360714 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][C:12]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[N:11](CC2C=CC=CC=2)[CH2:10][C:9]1([CH3:26])[CH3:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:17][C:12]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[NH:11][CH2:10][C:9]1([CH3:26])[CH3:25])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 866803366-Benzyl-8,8-dimethyl-6,9-diaza-spiro[4.5]decane-9-carboxylic acid tert-butyl ester

Product 1

HCID 86680337tert-Butyl 8,8-dimethyl-6,9-diazaspiro[4.5]decane-9-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 7.58 g of 6-benzyl-8,8-dimethyl-6,9-diaza-spiro[4.5]decane-9-carboxylic acid tert-butyl ester in 140 ml of methanol was added 1.13 g Palladium on charcoal (10%) and the mixture was hydrogenated at r.t. and ambient pressure for 16 h. The catalyst was removed by filtration over celite and the filtrate was concentrated in vacuo to yield 5.38 g (95%) of the title compound, which was used without further purification.

Workup

  1. customwas hydrogenated at r.t.
  2. customThe catalyst was removed by filtration over celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4cad10c6e66b40da812f9e8ee6aaf399
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

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