Reaktion #638855

Reaktionsgleichung

Water

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

tert-butyl(±)-[(1R,5R,6R)-6-{[(tert-butoxycarbonyl)amino]methyl}-3-{[(4-methoxybenzyl)oxy]methyl}bicyclo[3.2.0]hept-3-en-6-yl]acetate

→

Tert-butyl(±)-[(1R,5R,6R)-6-{[(tert-butoxycarbonyl)amino]methyl}-3-(hydroxymethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at this temperature 0° C. for 1 hour
2. 2
   workup.STIRRINGfurther stirred at room temperature for 1 hour
3. 3
   SonstigeThen, the reaction was terminated by the addition of a saturated aqueous solution of sodium bicarbonate
4. 4
   Extraktionfollowed by extraction with methylene chloride
5. 5
   WaschenThe organic layer was washed with water
6. 6
   Trocknena saturated aqueous solution of sodium bicarbonate, and saturated saline and dried over anhydrous sodium sulfate
7. 7
   FiltrationThe residue was filtered
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   SonstigeThen, the obtained crude product
10. 10
    Sonstigewas purified by silica gel column chromatography
11. 11
    Sonstigeto obtain the compound of interest as an oil substance (571 mg, 64%)

Vorschrift

Water (1.4 mL) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (831 mg, 3.66 mmol) were added to a methylene chloride solution (25 mL) of tert-butyl(±)-[(1R,5R,6R)-6-{[(tert-butoxycarbonyl)amino]methyl}-3-{[(4-methoxybenzyl)oxy]methyl}bicyclo[3.2.0]hept-3-en-6-yl]acetate (1.19 g, 2.44 mmol) with stirring at 0° C. The mixture was stirred at this temperature 0° C. for 1 hour and further stirred at room temperature for 1 hour. Then, the reaction was terminated by the addition of a saturated aqueous solution of sodium bicarbonate, followed by extraction with methylene chloride. The organic layer was washed with water, a saturated aqueous solution of sodium bicarbonate, and saturated saline and dried over anhydrous sodium sulfate. The residue was filtered and concentrated under reduced pressure. Then, the obtained crude product was purified by silica gel column chromatography to obtain the compound of interest as an oil substance (571 mg, 64%).

Quelle