methyl 1-[methyl(N-{[(phenylmethyl)oxy]carbonyl}glycyl)amino]cyclopropanecarboxylate → 4-Methyl-4,7-diazaspiro[2.5]octane-5,8-dione
Reaction equation
[CH3:1][N:2]([C:10](=[O:23])[CH2:11][NH:12][C:13](OCC1C=CC=CC=1)=[O:14])[C:3]1(C(OC)=O)[CH2:5][CH2:4]1>CO>[CH3:1][N:2]1[C:10](=[O:23])[CH2:11][NH:12][C:13](=[O:14])[C:3]21[CH2:5][CH2:4]2Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Methyl 1-[methyl(N-{[(phenylmethyl)oxy]carbonyl}glycyl)amino]cyclopropanecarboxylate (3.66 g, 11.42 mmol) was dissolved in 50 mL of MeOH, degassed and placed under argon. 10% Pd/C (2.04 g) was added, and the contents were thoroughly degassed and placed under a hydrogen balloon for 2 h. The contents were then degassed, and the Pd/C was removed by filtration through Celite, washing with MeOH. The filtrate was concentrated in vacuo. The residue was dissolved in MeOH (100 mL) and heated to 60° C. with stirring for 4 h. The solvent was removed in vacuo to provide pure 4-methyl-4,7-diazaspiro[2.5]octane-5,8-dione (1.76 g, 99%). LCMS: (M+H)+: 155.1.
Workup
- customdegassed
- addition10% Pd/C (2.04 g) was added
- customthe contents were thoroughly degassed
- customfor 2 h
- customThe contents were then degassed
- customthe Pd/C was removed by filtration through Celite
- washwashing with MeOH
- concentrationThe filtrate was concentrated in vacuo
- dissolutionThe residue was dissolved in MeOH (100 mL)
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-779ee23c35e54e05b5be7d654d78593a
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893056B2
Reaction notes
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