Reaktion #468568

Reaktionsgleichung

1-tert-butoxycarbonyl-4-methyl-5-nitrobenzimidazole

ammonium formate

→

5-amino-1-tert-butoxycarbonyl-4-methylbenzimidazole

Lösungsmittel

methanol

ethylacetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered on Celite, with a methanol
2. 2
   Waschenwash of the solids
3. 3
   SonstigeThe filtrate is rotary evaporated
4. 4
   Sonstigethe residue partitioned between water and ethyl acetate
5. 5
   WaschenThe organic layer is washed with saturated ammonium chloride
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Sonstigerotary evaporated

Vorschrift

5-Amino-1-tert-butoxycarbonyl-4-methylbenzimidzole. To a solution of 8 g of 1-tert-butoxycarbonyl-4-methyl-5-nitrobenzimidazole in 40 mL of methanol and 400 mL of ethylacetate are added 500 mg of 10% palladium-on-carbon and 7.27 g of ammonium formate. The mixture is stirred at 50° C. for 2 hours, then filtered on Celite, with a methanol wash of the solids. The filtrate is rotary evaporated and the residue partitioned between water and ethyl acetate. The organic layer is washed with saturated ammonium chloride, dried over magnesium sulfate, filtered and rotary evaporated to afford 5-amino-1-tert-butoxycarbonyl-4-methylbenzimidazole as an off-white solid.

Quelle