Reacción #988966

Ecuación de reacción

benzoyl chloride

compound

(1R,3R,4S,6R,7R)-7-Hydroxy-6-hydroxymethyl-3-methoxy-2-oxa-5-aza-bicyclo[2,2,1]heptane-5-carboxylic acid benzyl ester

t-butyldimethylsilyl chloride

water

→

desired title compound

Rendimiento 86.6%

(1R,3S,4S,6R,7R)-7-Benzyloxy-6-t-butyldimethylsilyloxymethyl-3-methoxy-2-oxa-5-aza-bicyclo[2,2,1]heptane-5-carboxylic acid benzyl ester

Rendimiento 86.6%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred at 0° C. for 1 hour
2. 2
   Extracciónat 0° C. and the mixture was extracted with ethyl acetate
3. 3
   Lavadothe organic layer was washed with saturated brine (20 mL)
4. 4
   Secadodried with anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONby distilling off of the solvent under reduced pressure
6. 6
   OtroThe residue was purified

Procedimiento

The compound (152 mg, 0.49 mmol) synthesized in Example 7 (7b) was dissolved in pyridine (4 mL) and t-butyldimethylsilyl chloride (82 mg, 0.54 mmol) was added thereto, followed by stirring of the mixture at 0° C. for 3 hours. After it was confirmed by TLC that the raw material was no longer present, benzoyl chloride (86 μL, 0.74 mmol) was added and the mixture was stirred at 0° C. for 1 hour. After water (20 mL) was added thereto at 0° C. and the mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine (20 mL) and dried with anhydrous sodium sulfate, followed by distilling off of the solvent under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 10:1, V/V) to obtain the desired title compound (218 mg, yield 84%) as a colorless oil.

Fuente