Sodium Azide → 11-Amino-1-undecanol

11-bromoundecan-1-ol (the compound 31) (15.1 g) was dissolved in 250 ml of acetonitrile, and 15.7 g of sodium azide was added to that, followed by 18-hour reaction caused by refluxing. After cooled down to room temperature, the solid components were removed by filtration. The solvent of the filtrate was distilled away under reduced pressure, to obtain 13.9 g of a transparent, viscous liquid. Of this liquid, 8.34 g was dissolved in 60 ml of THF distilled from calcium hydride in a nitrogen atmosphere, and was cooled in an ice bath. Lithium aluminum hydride (2.53 g) was then dried, and was dissolved in 250 ml of THF. The resultant was dripped, and was then stirred in an ice bath for one hour. After that, 2.5 ml of ion-exchange water, 3.5 ml of 15 wt % aqueous sodium hydride solution, and 7.5 ml of ion-exchange water were added so as to stop reactions. The precipitate generated was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure. After the filtrate was dried under reduced pressure, the dried filtrate was dissolved in 60 ml of THF, and the same volume of heptane was added to that. The precipitate generated was collected by filtration, to obtain 5.1 g of a white solid 32.

1. waitfollowed by 18-hour
2. customreaction
3. temperatureby refluxing
4. customthe solid components were removed by filtration
5. distillationThe solvent of the filtrate was distilled away under reduced pressure
6. customto obtain 13.9 g of a transparent, viscous liquid
7. distillationdistilled from calcium hydride in a nitrogen atmosphere
8. temperaturewas cooled in an ice bath
9. dry with materialLithium aluminum hydride (2.53 g) was then dried
10. dissolutionwas dissolved in 250 ml of THF
11. additionAfter that, 2.5 ml of ion-exchange water, 3.5 ml of 15 wt % aqueous sodium hydride solution, and 7.5 ml of ion-exchange water were added so as
12. customThe precipitate generated was removed by filtration
13. distillationthe solvent of the filtrate was distilled away under reduced pressure
14. customAfter the filtrate was dried under reduced pressure
15. dissolutionthe dried filtrate was dissolved in 60 ml of THF
16. additionthe same volume of heptane was added to that
17. filtrationThe precipitate generated was collected by filtration

ORD record

ord-7a6ad710c2084428862adfd84858ad82

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08475685B2