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

HRID 271584Notes

Reaction equation

HRID 271584 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:19][CH2:18][C:11]2([NH:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.[C:22](=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([NH:15][C:14](=[O:16])[N:13]([CH3:22])[C:12]2=[O:17])[CH2:18][CH2:19]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3629994Tert-butyl 2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 18931276Tert-butyl 3-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylateYield 103.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2,4-dioxo-1,3,8-triaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester (3.60 g, 13 mmol) in DMSO (30 ml), MeI (2.27 g, 16 mmol) and potassium carbonate (2.40 g, 17 mmol) are added at ambient temperature. The mixture is stirred for 18 h at ambient temperature. The reaction mixture is quenched with water and extracted with AcOEt. The combined extracts are washed with brine, dried over magnesium sulfate, filtrated and evaporated to afford 3.8 g of the desired product.

Workup

  1. customThe reaction mixture is quenched with water
  2. extractionextracted with AcOEt
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltrated
  6. customevaporated

Sources & evidence

ORD record
ord-9b78b32805ec423682b2cb56fe5700e5
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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