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

HRID 1598999Notes

Reaction equation

HRID 1598999 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[NH:3]1.[CH3:20]OS(OC)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:1]=[C:2]1[N:6]([CH3:20])[C:5](=[O:7])[C:4]2([CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[NH:3]1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 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 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of tert-butyl 2,4-dioxo-1,3,8-triaza-8-spiro[4.5]decane-carboxylate (4.9 g, 18.2 mmol), dimethylsulfate (2.9 g, 23 mmol), potassium carbonate (10.8 g, 78.3 mmol) and DMF (60 mL) was stirred approximately 60 hours at 25° C. The mixture was concentrated and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, washed with water (3×), dried (Na2SO4), filtered and concentrated to give tert-butyl 2,4-dioxo-3-methyl-1,3,8-triaza-8-spiro[4.5]decanecarboxylate (4.7 g, 16.6 mmol), m.p. 206°-208° C.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. washwashed with water (3×)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e517a01d568247c3b7219a2e4c42aafb
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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