Reaktion #92722

Reaktionsgleichung

methyl 6,6a-dihydro-1aH-indeno[1,2-b]oxirene-1a-carboxylate

sodium azide

ammonium chloride

sodium hydrogen carbonate

→

methyl rac-(1R,2R)-1-amino-2-hydroxyindane-1-carboxylate

Ausbeute 93.6%

Lösungsmittel

water

methanol

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigea layer separation operation
2. 2
   Trocknenthe organic layer was dried over anhydrous magnesium sulfate
3. 3
   workup.ADDITIONTo a solution of the obtained intermediate product in ethyl acetate-methanol was added 61 mg of 10% palladium-carbon (wet)
4. 4
   workup.STIRRINGby stirring for 6 hours under a hydrogen atmosphere
5. 5
   FiltrationThe reaction mixture was filtered over Celite
6. 6
   Sonstigethe solvent was then evaporated under reduced pressure

Vorschrift

To 500 mg of methyl 6,6a-dihydro-1aH-indeno[1,2-b]oxirene-1a-carboxylate were added 860 mg of sodium azide, 309 mg of ammonium chloride, 4 ml of methanol, and 0.5 ml of water, followed by stirring at 80° C. for 2 hours. To the reaction mixture were added a saturated aqueous sodium hydrogen carbonate solution, water, and ethyl acetate to carry out a layer separation operation, and the organic layer was dried over anhydrous magnesium sulfate. To a solution of the obtained intermediate product in ethyl acetate-methanol was added 61 mg of 10% palladium-carbon (wet), followed by stirring for 6 hours under a hydrogen atmosphere. The reaction mixture was filtered over Celite and the solvent was then evaporated under reduced pressure to obtain 0.51 g of methyl rac-(1R,2R)-1-amino-2-hydroxyindane-1-carboxylate.

Quelle