Reacción #453012

Ecuación de reacción

5-bromo-3-hydroxypyridine

Triphenylphosphine

DEAD

1-BOC-2-(S)-azetidinemethanol

→

title compound

Rendimiento 47.7%

5-bromo-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine

Rendimiento 47.7%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGthe reaction rnixture was stirred for 40 hours at room temperature
3. 3
   OtroThe volatiles were removed under vacuum
4. 4
   Otrothe residue was triturated with hexane
5. 5
   OtroThe hexane was removed
6. 6
   Otrothe residue was chromatographed on a silica gel column
7. 7
   Lavadoeluting with hexane:Et2O 10:1 to 10:2

Procedimiento

Triphenylphosphine (4.01 g, 15.3 mmol) and DEAD (2.43 mL, 15.3 mmol) were dissolved in 30 mL of THF at 0° C., and the mixture was stirred for for 10 minutes. Samples of 1-BOC-2-(S)-azetidinemethanol (2.86 g, 15.3 mmol), prepared as described above, and 5-bromo-3-hydroxypyridine (1.505 g, 10.2 mmol) were added, and the reaction rnixture was stirred for 40 hours at room temperature. The volatiles were removed under vacuum, and the residue was triturated with hexane. The hexane was removed, and the residue was chromatographed on a silica gel column, eluting with hexane:Et2O 10:1 to 10:2 to afford the title compound as a colorless oil (1.669 g). MS (CI/NH3) m/z 344 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.42 (s, 9H), 2.31 (m, 2H), 3.89 (m, 2H), 4.12 (m, 1H), 4.322 (m, 1H), 4.52 (m, 1H), 7.43 (m, 1H), 8.29 (m, 2H).

Fuente