N-methylhydroxylamine hydrochloride → 7-Acetyl-1,2-dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane

HRID 981113Notes

Reaction equation

HRID 981113 reaction equation
[CH2:1]([N:4]([CH2:8][C:9](=O)[CH3:10])[C:5](=[O:7])[CH3:6])[CH:2]=[CH2:3].C([O-])(=O)C.[Na+].Cl.[CH3:18][NH:19][OH:20]>O1CCOCC1.O>[C:5]([N:4]1[CH2:1][C:2]2([CH3:3])[CH:9]([CH2:10][O:20][N:19]2[CH3:18])[CH2:8]1)(=[O:7])[CH3:6]

Participants

6

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 15069994N-allyl-N-(2-oxopropyl)-acetamide

Product 1

HCID 150700177-Acetyl-1,2-dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

15.5 g (0.1 mol) of N-allyl-N-(2-oxopropyl)-acetamide 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-1528066a30484e81b48142fc3ccc924b
Source dataset
uspto-grants-1991_02
Patent number
US04990517

Reaction notes

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