Reaktion #1284666

Reaktionsgleichung

ammonium chloride

Potassium t-butoxide

2-(pyrid-3-yl)cyclohexanone

dimethylformamide

di-t-butyl diazodicarboxylate

→

2-(N,N'-di-t-butoxycarbonylhydrazino)-2-(pyrid-3-yl)cyclohexanone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate (2×25 ml)
2. 2
   WaschenThe combined organic extracts were successively washed with water (20 ml) and saturated brine (20 ml)
3. 3
   Trocknendried over sodium sulphate
4. 4
   EinengenConcentration in vacuo
5. 5
   Sonstigegave the crude product which
6. 6
   Sonstigewas recrystallised from petroleum ether (60°-80° C.; 150 ml)

Vorschrift

Potassium t-butoxide (3.7 g, 33 mmol) was added, in one portion, to a stirred solution of 2-(pyrid-3-yl)cyclohexanone (5.3 g, 30 mmol) in dimethylformamide (60 ml) at 0° C. After 60 minutes the dark red solution was treated with di-t-butyl diazodicarboxylate (7.6 g, 33 mmol) over 5 minutes. The mixture was then allowed to warm to 20° C. over 1 hour, poured into saturated ammonium chloride solution (50 ml) and extracted with ethyl acetate (2×25 ml). The combined organic extracts were successively washed with water (20 ml) and saturated brine (20 ml) and dried over sodium sulphate. Concentration in vacuo gave the crude product which was recrystallised from petroleum ether (60°-80° C.; 150 ml) to give 2-(N,N'-di-t-butoxycarbonylhydrazino)-2-(pyrid-3-yl)cyclohexanone (7.1 g, 17.5 mmol), m.p. 123°-125° C.;

Quelle