Acetic Acid → 4-Methylene-2-oxo-3-phenyl-1-oxa-3,8-diazaspiro[4,5]decane
Reaction equation
C([N:3]1[CH2:20][CH2:19][C:6]2([O:10][C:9](=[O:11])[N:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:7]2=[CH2:18])[CH2:5][CH2:4]1)=O.O.NN.C(O)(=O)C>C(O)C>[CH2:18]=[C:7]1[C:6]2([CH2:19][CH2:20][NH:3][CH2:4][CH2:5]2)[O:10][C:9](=[O:11])[N:8]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
Procedure
A solution containing 5.4 g of 8-formyl-4-methylene-2-oxo-3-phenyl-1-oxa-3,8-diazaspiro[4,5]decane, 3.0 g of hydrazine monohydrate and 3.6 g of acetic acid in 54 ml of aqueous ethanol of 60% by volume concentration is stirred under argon at a temperature of 62°-65° C. The reaction is followed by TLC. After termination of the reaction the mixture is evaporated under reduced pressure. After taking up the residue in chloroform and saturated aqueous sodium hydrogen carbonate solution, the chloroformic phase is separated, washed to neutral, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The crude product obtained is recrystallized from ethyl acetate under clarifying by activated carbon to give the title compound in 41.0% yield, m.p.: 185°-186° C.
Workup
- concentrationby volume concentration
- customAfter termination of the reaction the mixture
- customis evaporated under reduced pressure
- customsaturated aqueous sodium hydrogen carbonate solution, the chloroformic phase is separated
- washwashed to neutral,
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated under reduced pressure
- customThe crude product obtained
- customis recrystallized from ethyl acetate under clarifying by activated carbon
Sources & evidence
- ORD record
- ord-46c053b4f2f64a24ac72f036107fc2ef
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05157038
Reaction notes
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