Reacción #467326

Ecuación de reacción

2-benzylamino-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

ammonium formate

→

2-amino-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

Rendimiento 45.9%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for 3.5 hours
2. 2
   FiltraciónThe insoluble material was filtered off
3. 3
   Otrothe solvent was evaporated in vacuo
4. 4
   OtroThe residue Has partitioned between ethyl acetate and sat. NaHCO3
5. 5
   LavadoThe organic layer was washed with brine
6. 6
   OtroThe dried solvent was evaporated in vacuo
7. 7
   OtroThe residue was purified by chromatography on silica gel

Procedimiento

A mixture of 2-benzylamino-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (3.15 g), ammonium formate (4.41 g) and Pd/C (0.15 g) in ethanol (EtOH) (40 ml) was refluxed for 3.5 hours. The insoluble material was filtered off and the solvent was evaporated in vacuo. The residue Has partitioned between ethyl acetate and sat. NaHCO3. The organic layer was washed with brine. The dried solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 2-amino-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (1.18 g).

Fuente