Reacción #486708

Ecuación de reacción

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

methanesulfonyl chloride

→

(4S)-1-(tert-Butyloxycarbonyl)-4-(methanesulfonyloxy)-L-Proline tert-Butyl Ester

Disolventes

ethyl acetate

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto reach room temperature
2. 2
   Lavadowashed with saturated sodium hydrogencarbonate solution, 1 M citric acid, water
3. 3
   Otrodried (Na2 SO4)
4. 4
   Otroevaporated
5. 5
   OtroThe crude product was purified by flash silica gel chromatography
6. 6
   Lavadoeluting with 15% acetone/hexane

Procedimiento

To a solution of (4S)-1-(tert-butyloxycarbonyl)-4-hydroxy-L-proline tert-butyl ester (313 mg, 1.09 mmol) in pyridine (2.0 mL) cooled to 0° C. was added methanesulfonyl chloride (0.17 mL, 2.18 mmol). The reaction mixture was allowed to reach room temperature, and after 2 hours was diluted with ethyl acetate (100 mL), washed with saturated sodium hydrogencarbonate solution, 1 M citric acid, water, dried (Na2 SO4), and evaporated. The crude product was purified by flash silica gel chromatography eluting with 15% acetone/hexane; yield 251 mg (52% over 2 steps). 400 MHz 1H NMR (CDCl3): δ1.42-1.48 (3s, 18H); 2.38-2.50 (m, 2H); 2.99 (2s, 3H); 3.69-3.79 (m, 2H); 5.22 (m, 1H).

Fuente