Hydrochloric Acid → [1-Benzyl-3-(hydroxymethyl)azetidin-3-YL]methanol

温度

100 °C

18.1 g of 1A and 11.7 g of benzylamine were mixed with 5 ml of water and the resulting mixture was stirred at 100° C. After 4 hours the solution was allowed to cool to ambient temperature and 13.8 ml of 36% (w/w) hydrochloric acid was added. The resulting mixture was stirred at 60° C. After 2 hours the solution was again allowed to cool to room temperature and then washed with dichloromethane to remove by-products. The aqueous layer was made alkaline by the addition of a solution of 5.5 g of sodium hydroxide in 10 ml of water and stirred at 100° C. for 1 hour. After cooling to ambient temperature the pH of the mixture was raised by addition of another solution of 5.5 g of sodium hydroxide in 10 ml of water and washed with hexane to remove benzylamine. The water was evaporated under reduced pressure, and the solid residue was taken up in dichloromethane. Inorganic salts, which remained undissolved, were removed by filtration, and the dichloromethane was evaporated in vacuo, leaving 1, as a white crystalline solid.

1. temperatureto cool to ambient temperature
2. stirringThe resulting mixture was stirred at 60° C
3. waitAfter 2 hours the solution was again allowed
4. temperatureto cool to room temperature
5. washwashed with dichloromethane
6. customto remove by-products
7. additionby the addition of a solution of 5.5 g of sodium hydroxide in 10 ml of water
8. stirringstirred at 100° C. for 1 hour
9. temperatureAfter cooling to ambient temperature the pH of the mixture
10. temperaturewas raised by addition of another solution of 5.5 g of sodium hydroxide in 10 ml of water
11. washwashed with hexane
12. customto remove benzylamine
13. customThe water was evaporated under reduced pressure
14. customwere removed by filtration
15. customthe dichloromethane was evaporated in vacuo
16. customleaving 1

ORDレコード

ord-c4cd9b50b8c84c5e8537f76c629da15e

出典データセット

uspto-grants-1987_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04665197