Hydrochloric Acid → N-t-butyl-3-hydroxy-1-pentanesulfonamide

Temperature

-50 °C

Under nitrogen atmosphere, a solution (520 ml) of 1.6 M n-butyl lithium in hexane was added slowly to a solution (480 ml) of diisopropylamine (120 ml) in tetrahydrofuran at −60 to −50° C. and the solution was stirred for 1 hour in an ice bath. The solution was cooled to −50° C. and a solution (100 ml) of N-t-butylmethane-sulfonamide (60.0 g) in tetrahydrofuran was added dropwise thereto taking 45 minutes. The temperature of the solution was raised to 0° C. taking 1 hour and the solution was stirred for 45 minutes in an ice bath. It was cooled to −40° C. and a solution (50 ml) of butylene oxide (42.9 g)in tetrahydrofuran was added thereto at −40 to −30° C. The temperature of the solution was raised slowly to room temperature and the solution was stirred overnight. The reaction was stopped by adding water in an ice bath. The solution was made acidic with dilute hydrochloric acid and the tetrahydrofuran layer was separated. The aqueous layer was extracted with chloroform. The tetrahydrofuran and aqueous layers were independently washed with saturated brine. The organic layers were combined, dried over sodium sulfate, and concentrated under reduced pressure. To the residue thus obtained was added t-butyl methyl ether (89 g). Crystallization was initiated by further adding hexane (200 ml). The crystals were collected by filtration, washed with a small amount of a mixed solution of t-butyl methyl ether and hexane (½), and dried under reduced pressure. Thus, N-t-butyl-3-hydroxy-1-pentanesulfonamide (60.6 g) was obtained.

1. waitthereto taking 45 minutes
2. temperatureThe temperature of the solution was raised to 0° C.
3. waittaking 1 hour
4. stirringthe solution was stirred for 45 minutes in an ice bath
5. temperatureIt was cooled to −40° C.
6. customat −40 to −30° C
7. temperatureThe temperature of the solution was raised slowly to room temperature
8. stirringthe solution was stirred overnight
9. customthe tetrahydrofuran layer was separated
10. extractionThe aqueous layer was extracted with chloroform
11. washThe tetrahydrofuran and aqueous layers were independently washed with saturated brine
12. dry with materialdried over sodium sulfate
13. concentrationconcentrated under reduced pressure
14. customTo the residue thus obtained
15. customCrystallization
16. additionby further adding hexane (200 ml)
17. filtrationThe crystals were collected by filtration
18. washwashed with a small amount of a mixed solution of t-butyl methyl ether and hexane (½)
19. customdried under reduced pressure

ORD record

ord-6f263adace2a4b11bc39de3d99935b16

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06420409B1