Reaktion #305241

Reaktionsgleichung

O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.0]octane-7-carboxylic acid

N,O-dimethylhydroxylamine hydrochloride

diisopropylethylamine

sodium bicarbonate

→

N-methoxy-N-methyl-3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.0]octane-7-carboxamide

Ausbeute 86.3%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate (100 mL)
2. 2
   WaschenThe organic layer was washed with water (200 mL)
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   Einengenconcentrated by rotary evaporation
5. 5
   Sonstigepurified by silica gel flash column chromatography

Vorschrift

To a mixture of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.0]octane-7-carboxylic acid (0.930 g, 3.65 mmol), N,O-dimethylhydroxylamine hydrochloride (0.71 g, 7.3 mmol) and diisopropylethylamine (DIPEA) (3.24 mL, 18.3 mmol) in N,N-dimethylformamide (DMF) (50 mL) was added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (2.07 g, 5.48 mmol), and the mixture was stirred at ambient temperature overnight. The reaction was poured into saturated aqueous sodium bicarbonate (100 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with water (200 mL), dried over anhydrous sodium sulfate, concentrated by rotary evaporation and purified by silica gel flash column chromatography, to obtain 0.94 g (86% yield) of the N-methoxy-N-methyl-3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.0]octane-7-carboxamide, as an oil (1H NMR (CDCl3, 300 MHz): δ 3.69 (s, 3H), 3.6-3.42 (m, 2H), 3.36-3.05 (m, 3H), 3.18 (s, 3H), 2.82-2.57 (m, 2H), 2.08-2.02 (m, 2H), 1.82-1.65 (m, 2H), 1.46 (d, 9H); MS (m/z: 299 (M+1), 243 (M+1-56)).

Quelle