تفاعل #2018505

معادلة التفاعل

ethyl acetate

4-fluoro-2-(1-methylcyclohexyl)-5-nitrophenyl methyl carbonate

ammonium formate

→

5-amino-4-fluoro-2-(1-methylcyclohexyl)phenyl methyl carbonate

المردود 82.1%

المذيبات

CH3OH

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONadded to the above reaction mixture at room temperature
2. 2
   أخرىis consumed
3. 3
   ترشيحThe mixture was filtrated
4. 4
   أخرىthe filtrate was evaporated under vacuum
5. 5
   أخرىThe residue was purified by column chromatography on silica gel
6. 6
   workup.ADDITIONdiluted with hexane

الإجراء التجريبي

To a solution of 4-fluoro-2-(1-methylcyclohexyl)-5-nitrophenyl methyl carbonate 24.1 g, 77.5 mmol) in 220 mL of CH3OH was added Pd/C 10%, 9.6 g, then ammonium formate (26.7 g, 445 mmol) was portion-wise added to the above reaction mixture at room temperature until starting material is consumed. The mixture was filtrated and the filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel diluted with hexane:ethyl acetate=50:1 to give 5-amino-4-fluoro-2-(1-methylcyclohexyl)phenyl methyl carbonate as a red brown oil (17.9 g, 82% yield). 1H NMR (400 MHz, CDCl3) δ 6.99 (d, J=13.6 Hz, 1H), 6.51 (d, J=8.4 Hz, 1H), 3.89 (s, 3H), 3.43 (brs, 2H), 1.96-1.91 (m, 2H), 1.58-1.38 (m, 8H), 1.18 (s, 3H): MS m/z: 281.9 [M+H]+

المصدر