Methanol → Tert-butyl 2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

HRID 271583Notes

Reaction equation

HRID 271583 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15](=[O:18])([O-])[O-].[NH4+:19].[NH4+:20].[C-]#N.[Na+].[CH3:24][OH:25]>O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([NH:20][C:24](=[O:25])[NH:19][C:15]2=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8929Sodium CyanideHCID 517111Ammonium CarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 3629994Tert-butyl 2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (30.0 g, 151 mmol) in MeOH (100 ml), H2O (40 ml), ammonium carbonate (331 mmol) and sodium cyanide (226 mmol) in H2O (60 ml) are added successively at ambient temperature. The reaction mixture is stirred at ambient temperature for 18 h to give precipitates, which are filtered off and washed with H2O and ether on the filter.

Workup

  1. customto give
  2. customprecipitates
  3. filtrationwhich are filtered off
  4. washwashed with H2O and ether on the filter

Sources & evidence

ORD record
ord-1ca84f2ff9f141c9b27bb55cbb4e946b
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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