Cyclohexanone → 1-Oxa-4-azaspiro[4.5]decane-4-ethanol

Participants

Reaction Conditions

Reaction Steps

To a 50 mL flask containing diethanolamine (9,7 mL, 100 mmol) was added cyclohexanone (10,4 mL, 100 mmol, 1 eq.) and potassium carbonate (pulverized and dried at 160° C., 13,8 g, 100 mmol, 1 eq.). The reaction was stirred at 80° C. for 12 h. The reaction was cooled to room temperature and diluted with dichloromethane before filtering off potassium carbonate. The crude mixture diluted in cyclohexane was washed with water at 0° C. Drying with sodium sulfate and evaporation afforded the title product (8,4 g, 45% yield). 1H NMR (CDCl3, 400 MHz) d?(ppm): 3,91 (t, J=6,7 Hz, 2H); 3,60 (m, 2H); 3,00 (t, J=6,7 Hz, 2H); 2,70 (t, J=5,3 Hz, 2H); 1,72-1,50 (m, 7H); 1,43-1,30 (m, 2H); 1,21-1,04 (m, 1H). 13C NMR (CDCl3, 129,9 MHz) d?(ppm): 94,9; 63,2; 59,2; 50,3; 49,0; 32,6 (2C); 25,6; 23,3 (2C).

Provenance & Evidence