10,11-dihydro-5H-dibenzo[b,f]azepin-10-o

Synthesis

21737-58-6

4014-77-1

The general procedure for the synthesis of 10,11-dihydro-5H-dibenzo[b,f]azepin-10-ol from 5H-dibenzo[b,f]azepin-10(11H)-one was as follows: 5H-dibenzo[b,f]azepin-10(11H)-one (350.0 g, 1.67 mol) was suspended in water (0.7 L) and methanol (2.8 L) in a mixed solvents. Sodium borohydride (76 g, 2.0 mol) was added in batches over 10 min without cooling and the reaction mixture was stirred continuously at 45 °C for 1 h. The reaction was completed by the addition of acetone (1.0 g, 2.0 mol). Upon completion of the reaction, acetone (350 mL) was added cautiously to quench the reaction and the reaction mixture was subsequently concentrated to a smaller volume. The target product was precipitated by the addition of water (700 mL) and the precipitate was collected and dried at 60-65 °C to afford (S)-10,11-dihydro-5H-dibenzo[b,f]azepin-10-ol (315 g, 89.0% yield) as an off-white solid with a purity of >98%.

References