Hydrogen Peroxide → Tert-butyl 3-(aminocarbonyl)-3-[benzyl(methyl)amino]azetidine-1-carboxylate
Reaction equation
[OH-:1].[Na+].[CH2:3]([N:10]([CH3:20])[C:11]1([C:18]#[N:19])[CH2:14][N:13]([C:15]([O-:17])=[O:16])[CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.OO>C(O)C>[NH2:19][C:18]([C:11]1([N:10]([CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:20])[CH2:14][N:13]([C:15]([O:17][C:4]([CH3:9])([CH3:5])[CH3:3])=[O:16])[CH2:12]1)=[O:1]Participants
Procedure
A 1M solution of sodium hydroxide (12.5 ml, 12.5 mmol) at 0° C. was added dropwise to a solution of 3-[benzyl(methyl)amino]-3-cyanoazetidine-1-carboxylate (800 mg, 2.66 mmol) in ethanol (25 ml). Hydrogen peroxide 30% wt (1 ml) was then added and the reaction mixture was allowed to stir at room temperature overnight. After removal of solvent under reduced pressure, the remaining aqueous layer was extracted with ethyl acetate (×2) and the combined organic layers washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford tert-butyl 3-(aminocarbonyl)-3-[benzyl(methyl)amino]azetidine-1-carboxylate (702 mg, 87%) as a white solid, used without any further purification in the next step; 1H NMR Spectrum: (CDCl3) 1.45 (s, 9H), 2.27 (s, 3H), 3.61 (s, 2H), 4.07 (d, 2H), 4.22 (brd, 2H), 5.51 (brs, 1H), 6.70 (brs, 1H), 7.26-7.36 (m, 5H); Mass Spectrum: (M+H)+ 320.
Workup
- customAfter removal of solvent under reduced pressure
- extractionthe remaining aqueous layer was extracted with ethyl acetate (×2)
- washthe combined organic layers washed with water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-cb274ce43a55455c9e44b43b88b36447
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07632840B2
Reaction notes
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