Reacción #486709

Ecuación de reacción

(4S)-1-(tert-butyloxycarbonyl)-4-(methanesulfonyloxy)-L-proline tert-butyl ester

sodium azide

→

azide

(4R)-1-(tert-Butyloxycarbonyl)-4-azido-L-Proline tert-Butyl Ester

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe cooled reaction mixture
2. 2
   Otrowas evaporated
3. 3
   Otropartitioned between diluted ethyl acetate and water
4. 4
   LavadoThe organic layer was washed with water, 0.1N hydrochloric acid, water, saturated brine solution
5. 5
   Secadodried (Na2SO4)
6. 6
   Otroevaporated
7. 7
   Lavadoeluting with 10% ethyl acetate/hexane

Procedimiento

A mixture of (4S)-1-(tert-butyloxycarbonyl)-4-(methanesulfonyloxy)-L-proline tert-butyl ester (250 mg, 0.684 mmol) and sodium azide (222 mg, 3.42 mmol) in N,N-dimethylformamide (1.5 mL) was stirred for 18 hours at 55° C. under a nitrogen atmosphere. The cooled reaction mixture was evaporated and partitioned between diluted ethyl acetate and water. The organic layer was washed with water, 0.1N hydrochloric acid, water, saturated brine solution, dried (Na2SO4), and evaporated. The crude product mixture was subjected to flash silica gel chromatography eluting with 10% ethyl acetate/hexane. The desired azide was obtained as a colorless oil; yield 196 mg (92%). 400 MHz 1H NMR (CDCl3): δ1.42-1.45 (3s, 18H); 2.11 (m, 1H); 2.22-2.36 (m, 1H); 3.68 (m, 1H); 4.12 (m, 1H).

Fuente