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