Water → Ethyl 2,8-dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane-7-carboxylate

HRID 36685

Reaction equation

HRID 36685 reaction equation
Cl.[CH3:2][NH:3][OH:4].C[O-].[Na+].[CH2:8]([N:11]([CH:17]([CH3:20])[CH:18]=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[CH2:10].O>CO.C1(C)C=CC=CC=1>[CH3:2][N:3]1[O:4][CH2:10][CH:9]2[CH:18]1[CH:17]([CH3:20])[N:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8]2

Participants

7

Reactant 4

HCID 962WaterHCID 77906N-methylhydroxylamine hydrochlorideHCID 10942334Sodium MethoxideHCID 15069993Ethyl N-allyl-N-(1-oxoprop-2-yl)-carbamate

Product 1

HCID 15070012Ethyl 2,8-dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane-7-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

A methanolic methylhydroxylamine solution is prepared from 16.4 g (0.2 mol) of N-methylhydroxylamine hydrochloride in 33 ml of absolute methanol and 36 g (0.2 mol) of 30% strength sodium methylate solution, and the solution formed is diluted with 130 ml of toluene and added dropwise to 354 g (0.17 mol) of N-allyl-N-(1-oxoprop-2-yl)-urethane in 250 ml of toluene, which is heated under reflux using a water separator. The mixture is heated under reflux overnight, the product is extracted with dilute hydrochloric acid and the hydrochloric acid solution is rendered alkaline with K2CO3 and extracted with CHCl3. The extract is dried over K2CO3 and concentrated and the residue is distilled.

Workup

  1. customthe solution formed
  2. temperatureis heated
  3. temperatureunder reflux
  4. temperatureThe mixture is heated
  5. temperatureunder reflux overnight
  6. extractionthe product is extracted with dilute hydrochloric acid
  7. extractionextracted with CHCl3
  8. dry with materialThe extract is dried over K2CO3
  9. concentrationconcentrated
  10. distillationthe residue is distilled

Sources & evidence

ORD record
ord-227c9b275f264cd383e3bb36421fbf18
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Linked notes

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