Acetonitrile → 5-Azaspiro[2.4]heptan-4-one, 7-amino-7-methyl-

HRID 1675192Notes

Reaction equation

HRID 1675192 reaction equation
C(#N)C.Cl.Cl.[NH2:6][C:7]([C:11]1([C:14]([OH:16])=O)[CH2:13][CH2:12]1)([CH3:10])[CH2:8][NH2:9].C[Si](C)(C)N[Si](C)(C)C>CO>[NH2:6][C:7]1([CH3:10])[C:11]2([CH2:13][CH2:12]2)[C:14](=[O:16])[NH:9][CH2:8]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 13838HexamethyldisilazaneHCID 574343681-(1,2-Diamino-1-methylethyl)-1-cyclopropanecarboxylate dihydrochloride

Product 1

HCID 552821195-Azaspiro[2.4]heptan-4-one, 7-amino-7-methyl-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To an acetonitrile solution (70 mL) of the crude product (800 mg, 3.46 mmol) of 1-(1,2-diamino-1-methylethyl)-1-cyclopropanecarboxylate dihydrochloride was added 1,1,1,3,3,3-hexamethyldisilazane (7.38 mL, 34.6 mmol), and the mixture was heated under reflux under a nitrogen atmosphere in an oil bath at 100° C. for 4 hours. Then the solution was cooled to room temperature, and to the solution was added methanol (70 mL). After that, the solvent was removed under reduced pressure. Thus a crude product of 7-amino-7-methyl-5-azaspiro[2.4]heptan-4-one was obtained as a light brown gum-like solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureThen the solution was cooled to room temperature
  3. customAfter that, the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3486e2102cc74134a5816f19c1149860
Source dataset
uspto-grants-2011_08
Patent number
US08003666B2

Reaction notes

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