N-methylhydroxylamine hydrochloride → Ethyl 2,4-dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane-7-carboxylate

HRID 36697

Reaction equation

HRID 36697 reaction equation
[CH2:1]([N:5]([CH2:11][CH:12]=O)[C:6](=[O:10])[O:7][CH2:8][CH3:9])[CH:2]=[CH:3][CH3:4].C([O-])(=O)C.[Na+].Cl.[CH3:20][NH:21][OH:22]>O1CCOCC1.O>[CH3:20][N:21]1[O:22][CH:3]([CH3:4])[CH:2]2[CH:12]1[CH2:11][N:5]([C:6]([O:7][CH2:8][CH3:9])=[O:10])[CH2:1]2

Participants

6

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 53690408ethyl N-(but-2-enyl)-N-(2-oxoethyl)-carbamate

Product 1

HCID 15070019Ethyl 2,4-dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane-7-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

18.4 g (0.1 mol) of ethyl N-(but-2-enyl)-N-(2-oxoethyl)-carbamate are dissolved in 100 ml of dioxane, and 9 g of anhydrous sodium acetate and 9 g (0.108 mol) of N-methylhydroxylamine hydrochloride in 10 ml of water are added. The mixture is heated under reflux overnight and cooled and the salts are filtered off with suction and washed with dioxane. The filtrate is concentrated, the residue is taken up in 100 ml of water and K2CO3 is added. The mixture is extracted with CHCl3, the extract is dried over K2CO3 and concentrated and the residue is distilled.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux overnight
  3. temperaturecooled
  4. filtrationthe salts are filtered off with suction
  5. washwashed with dioxane
  6. concentrationThe filtrate is concentrated
  7. additionK2CO3 is added
  8. extractionThe mixture is extracted with CHCl3
  9. dry with materialthe extract is dried over K2CO3
  10. concentrationconcentrated
  11. distillationthe residue is distilled

Sources & evidence

ORD record
ord-c363c3f6a8394ce3b9913ed620fe0370
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Linked notes

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