Water → Ethyl 2,5-dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane-7-carboxylate

HRID 36681

Reaction equation

HRID 36681 reaction equation
C[O-].[Na+].Cl.[CH3:5][NH:6][OH:7].[CH3:8][C:9](=[CH2:20])[CH2:10][N:11]([CH2:17][CH:18]=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13].O>CO.C1(C)C=CC=CC=1>[CH3:5][N:6]1[O:7][CH2:8][C:9]2([CH3:20])[CH:18]1[CH2:17][N:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:10]2

Participants

7

Reactant 4

HCID 962WaterHCID 77906N-methylhydroxylamine hydrochlorideHCID 10942334Sodium MethoxideHCID 15069992N-(2-Methylprop-2-enyl)-N-(2-oxoethyl)-urethane

Product 1

HCID 15070010Ethyl 2,5-dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane-7-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

21.7 g of 30% strength sodium methylate solution are added dropwise to 10 g (0.12 mol) of N-methylhydroxylamine hydrochloride in 26 ml of methanol. The sodium chloride is filtered off with suction and washed with 8 ml of methanol and 80 ml of toluene. This solution is added dropwise to 19.2 g (0.11 mol) of N-(2-methyl-prop-2-enyl)-N-(2-oxoethyl)-urethane, which is heated under reflux in 160 ml of toluene using a water separator. The mixture is heated under reflux overnight, the product is extracted with 160 ml of 10% strength hydrochloric acid and the hydrochloric acid solution is rendered alkaline with potassium carbonate and extracted with six portions, of 200 ml of CHCl3. The extracts are dried over K2CO3 and concentrated and the residue is distilled.

Workup

  1. filtrationThe sodium chloride is filtered off with suction
  2. washwashed with 8 ml of methanol and 80 ml of toluene
  3. temperatureis heated
  4. temperatureThe mixture is heated
  5. temperatureunder reflux overnight
  6. extractionthe product is extracted with 160 ml of 10% strength hydrochloric acid
  7. extractionextracted with six portions, of 200 ml of CHCl3
  8. dry with materialThe extracts are dried over K2CO3
  9. concentrationconcentrated
  10. distillationthe residue is distilled

Sources & evidence

ORD record
ord-7020e83ef5a14745ace0469bb96f35b9
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Linked notes

Loading…