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 2279182Notes

Reaction equation

HRID 2279182 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-ab0c23f7c4e349b799d50515d44d4598
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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