Hydrogen Peroxide → Tert-butyl 3-(aminocarbonyl)-3-[benzyl(methyl)amino]azetidine-1-carboxylate

HRID 1867739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867739
[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]

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 866169483-[Benzyl(methyl)amino]-3-cyanoazetidine-1-carboxylate

Produkt 1

HCID 69048045Tert-butyl 3-(aminocarbonyl)-3-[benzyl(methyl)amino]azetidine-1-carboxylateAusbeute 165,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customAfter removal of solvent under reduced pressure
  2. extractionthe remaining aqueous layer was extracted with ethyl acetate (×2)
  3. washthe combined organic layers washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cb274ce43a55455c9e44b43b88b36447
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632840B2

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