Reacción #1955358

Ecuación de reacción

compound

(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

sodium borohydride

ammonium chloride

→

desired title compound

Rendimiento 176.5%

(2R,3R,4R,5R)—N-Benzyloxycarbonyl-3-benzoyl-2,5-dihydroxymethyl-4-hydroxypyrrolidine

Rendimiento 176.5%

Disolventes

water

trifluoroacetic acid water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted with dichloromethane (30 mL)
2. 2
   Lavadothe organic layer was washed with saturated aqueous sodium hydrogencarbonate (20 mL) and saturated brine (20 mL)
3. 3
   Secadodried with anhydrous sodium sulfate
4. 4
   workup.DISTILLATIONby distilling off of the solvent under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethanol (15 mL)
6. 6
   Otrothe compound obtained
7. 7
   workup.ADDITIONwas added
8. 8
   workup.STIRRINGby stirring of the mixture at 0° C. for 20 minutes
9. 9
   workup.DISTILLATIONethanol was distilled off under reduced pressure
10. 10
    workup.ADDITIONAfter water (15 mL) was added
11. 11
    Extracciónthe mixture was extracted with ethyl acetate (15 mL)
12. 12
    Lavadothe organic layer was washed with saturated brine (15 mL)
13. 13
    Secadodried with anhydrous sodium sulfate
14. 14
    workup.DISTILLATIONby distilling off of the solvent under reduced pressure
15. 15
    OtroThe residue was purified

Procedimiento

The compound (997 mg, 1.89 mmol) synthesized in Example 7 (7c) was dissolved in trifluoroacetic acid:water (4:1, 12 mL) and the mixture was stirred at room temperature for 15 minutes. After water (20 mL) was added to the reaction mixture at 0° C. and the mixture was extracted with dichloromethane (30 mL), the organic layer was washed with saturated aqueous sodium hydrogencarbonate (20 mL) and saturated brine (20 mL) and dried with anhydrous sodium sulfate, followed by distilling off of the solvent under reduced pressure. The residue was dissolved in ethanol (15 mL) and the compound obtained by dissolving sodium borohydride (35.7 mg, 0.10 mmol) in water (5 mL) was added thereto, followed by stirring of the mixture at 0° C. for 20 minutes. After saturated aqueous ammonium chloride (2 mL) was added to the reaction mixture at 0° C., ethanol was distilled off under reduced pressure. After water (15 mL) was added thereto and the mixture was extracted with ethyl acetate (15 mL), the organic layer was washed with saturated brine (15 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, 2:1, V/V) to obtain the desired title compound (643 mg, yield 85%) as a colorless oil.

Fuente