1,1-Dimethyl-3-oxobutylammonium hydrogen oxalate → HCID 89852879, compound

HRID 1754398Notes

Reaction equation

HRID 1754398 reaction equation
[CH3:1][C:2]([CH2:4][C:5]([NH2:8])([CH3:7])[CH3:6])=[O:3].C(O)(C(O)=O)=O.O=[CH:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20]>CO>[CH3:6][C:5]1([CH3:7])[NH:8][CH:16]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:1][C:2](=[O:3])[CH2:4]1

Participants

4

Reactant 2

HCID 693601,1-Dimethyl-3-oxobutylammonium hydrogen oxalateHCID 83779Methyl 4-oxobutyrate

Product 1

HCID 89852879HCID 89852879, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

Diacetoneamine hydrogen oxalate (4.25 g) and methyl 4-oxobutanoate (2 g) were suspended in methanol (20 ml). The reaction mixture were stirred at 100° C. for three hours and then at room temperature overnight. It was then evaporated and the residue was purified by Combiflash chromatography (2.0 M ammonia methanol in dichloromethane=0-30%) to give methyl 3-(6,6-dimethyl-4-oxopiperidin-2-yl)propanoate (1.35 g, 37%).

Workup

  1. customat room temperature
  2. customovernight
  3. customIt was then evaporated
  4. customthe residue was purified by Combiflash chromatography (2.0 M ammonia methanol in dichloromethane=0-30%)

Sources & evidence

ORD record
ord-1bd3e24c67dc46b884ee6c505fdd2b24
Source dataset
uspto-grants-2015_10
Patent number
US09169249B2

Reaction notes

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