Ethyl chloroformate → HCID 86737272, compound

HRID 903581Notes

Reaction equation

HRID 903581 reaction equation
C12(CC(=O)OC(=O)C1)CCCCCC2.[CH3:15][O:16][C:17](=[O:30])[CH2:18][C:19]1([CH2:26][C:27]([OH:29])=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.ClC(OCC)=O.[N-:37]=[N+:38]=[N-:39].[Na+]>O.CC(C)=O.C(N(CC)CC)C.C1C=CC=CC=1.CO>[N-:37]=[N+:38]=[N-:39].[CH3:15][O:16][C:17](=[O:30])[CH2:18][C:19]1([CH2:26][C:27]([OH:29])=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

10

Reactant 4

HCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 20356202HCID 20356202, compoundHCID 45156304HCID 45156304, compound

Product 1

HCID 86737272HCID 86737272, compound

Reagents, catalysts & solvents 5

HCID 180AcetoneSolvent3×HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

13.7 g. 1,1-cycloheptane-diacetic anhydride are mixed with 2.36 g. anhydrous methanol in 10 ml. benzene and boiled under reflux for 2 hours. After evaporation in a vacuum, there are obtained 15.9 g. 1,1-cycloheptanediacetic acid monomethyl ester which is dissolved in 100 ml. anhydrous acetone and then, according to the description given in German Pat. No. 2,460,891, first mixed with 8.1 g. triethylamine in 30 ml. acetone, thereafter with 9.8 g. ethyl chloroformate in 30 ml. anhydrous acetone and finally with 6.5 g. sodium azide in 20 ml. water. After the reaction has taken place, the reaction mixture is extracted and the solution obtained of 1,1-cycloheptane-diacetic acid monomethyl ester azide in toluene is rearranged to give the isocyanate. The methyl 1-isocyanatomethyl-1-cycloheptane-acetate obtained is boiled under reflux for 3 hours in 20% hydrochloric acid. Upon concentration of the reaction mixture in a vacuum, 1-aminomethyl-1-cycloheptane-acetic acid separates out in the form of its hydrochloride. 32 g. 1-aminomethyl-1-cycloheptane-acetic acid hydrochloride, obtained from several reaction batches, and 45 g. anhydrous sodium acetate are heated under reflux for 5 hours in 300 ml. acetic anhydride. After cooling, inorganic salts are filtered off and the solvent is stripped off in a vacuum. Distillation of the residue gives N-acetyl-3-oxo-2-azaspiro[4,6]undecane in the form of a colourless oil; b.p. 125°-130° C./10-3 mm.Hg.

Workup

  1. temperatureunder reflux for 2 hours
  2. customAfter evaporation in a vacuum, there
  3. customare obtained 15.9 g
  4. addition2,460,891, first mixed with 8.1 g
  5. extractionthe reaction mixture is extracted

Sources & evidence

ORD record
ord-4d59f6e8b9964ba881acba34c48c8bf0
Source dataset
uspto-grants-1980_10
Patent number
US04228179

Reaction notes

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