Acetic Acid → HCID 87172952, compound

HRID 2167750Notes

Reaction equation

HRID 2167750 reaction equation
[CH3:1][O:2][N:3]1[C:8]([CH3:10])([CH3:9])[CH2:7][C:6]([C:16]#[N:17])([O:11][Si](C)(C)C)[CH2:5][C:4]1([CH3:19])[CH3:18].[CH3:20][C:21]([CH3:23])=O.S(=O)(=O)(O)[OH:25].[C:29]([O-:32])(O)=O.[Na+].[C:34](O)(=O)[CH3:35]>>[CH3:1][O:2][N:3]1[C:8]([CH3:10])([CH3:9])[CH2:7][C:6]2([O:11][C:21]([CH3:23])([CH3:20])[N:17]([CH2:34][CH:35]3[CH2:29][O:32]3)[C:16]2=[O:25])[CH2:5][C:4]1([CH3:19])[CH3:18]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 66832365HCID 66832365, compound

Product 1

HCID 87172952HCID 87172952, compound

Conditions

Temperature
70 °C

Procedure

1.0 g of 1-methoxy-2,2,6,6-tetramethyl-4-cyano-4-trimethylsilyloxypiperidine is dissolved in 1.76 g acetic acid and 0.48 g acetone is added. 0.7 g conc. sulfuric acid is added and the reaction mixture is stirred at 70° C. for 18 h while forming a deep red solution. The reaction mixture is added to 40 ml saturated NaHCO3 solution, and extracted with 40 ml ethyl acetate. The organic phase is washed with H2O and subsequently dried over sodium sulfate. The solvent is removed in vacuo to leave 0.87 g of a tan residue. After washing the residue with n-hexane, 8-methoxy-2,2,7,7,9,9-hexamethyl-1-oxa-3,8-diaza-spiro[4.5]decan-4-one is obtained as a white solid (0.46 g), mp. 230° C.

Workup

  1. customwhile forming a deep red solution
  2. extractionextracted with 40 ml ethyl acetate
  3. washThe organic phase is washed with H2O
  4. dry with materialsubsequently dried over sodium sulfate
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-eacba0824bf544c2b4980cf4a11b5fbb
Source dataset
uspto-grants-2015_06
Patent number
US09045480B2

Reaction notes

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