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

HRID 229510Notes

Reaction equation

HRID 229510 reaction equation
Cl.Cl.[NH2:3][C:4]([C:8]1([C:11]([OH:13])=O)[CH2:10][CH2:9]1)([CH3:7])[CH2:5][NH2:6].C[Si](C)(C)N[Si](C)(C)C.CO>C(#N)C>[NH2:3][C:4]1([CH3:7])[C:8]2([CH2:10][CH2:9]2)[C:11](=[O:13])[NH:6][CH2:5]1

Participants

5

Reactant 3

HCID 887MethanolHCID 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 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution (70 mL) of the crude 1-(1,2-diamino-1-methyl ethyl)-1-cyclopropanecarboxylic acid dihydrochloride (800 mg, 3.46 mmol) in acetonitrile was added 1,1,1,3,3,3-hexamethyldisilazane (7.38 mL, 34.6 mmol), and the mixture was heated under reflux in an oil bath at 100° C. for 4 hours under nitrogen atmosphere. The mixture was cooled to room temperature, and after adding methanol (70 mL), the solvent was removed by distillation under reduced pressure to obtain crude 7-amino-7-methyl-5-azaspiro[2.4]heptan-4-one as a pale brown gummy solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe mixture was cooled to room temperature
  3. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-3737c5c492294d79adf77c598d7d62a6
Source dataset
uspto-grants-2009_07
Patent number
US07563805B2

Reaction notes

Loading…