Реакция #1955356

Уравнение реакции

water

sodium hydrogencarbonate

benzyl chloroformate

compound

(1R,3S,4S,6R,7R)-7-Benzyloxy-6-hydroxymethyl-3-methoxy-2-oxa-5-aza-bicyclo[2,2,1]heptane

→

desired title compound

Выход 70.0%

(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

Выход 70.0%

Растворители

methanol

Условия реакции

Обработка

1. 1
   ДругоеAfter the catalyst was removed by celite filtration
2. 2
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
4. 4
   workup.STIRRINGby stirring of the mixture at 0° C. for 2 hours
5. 5
   Экстракцияat 0° C. and the mixture was extracted with ethyl acetate
6. 6
   Промывкаthe organic layer was washed with saturated brine (20 mL)
7. 7
   Сушкаdried with anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONby distilling off of the solvent under reduced pressure
9. 9
   ДругоеThe residue was purified

Методика

The compound (930 mg, 3.51 mmol) synthesized in Example 7 (7a) was dissolved in methanol (20 mL) and 20% palladium hydroxide-carbon (280 mg) was added thereto, followed by stirring of the mixture under a hydrogen atmosphere for 6 hours. After the catalyst was removed by celite filtration, the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate:saturated aqueous sodium hydrogencarbonate solution (2:1, 20 mL) and benzyl chloroformate (0.75 mL, 5.27 mmol) was added thereto, followed by stirring of the mixture at 0° C. for 2 hours. 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, 1:1-3:1, V/V) to obtain the desired title compound (759 mg, yield 70%) as a colorless solid.

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