Reacción #51646

Ecuación de reacción

Borohydride

2-{(1R)-1-Amino-2-[indol-3-yl]ethyl}-4-pheny-1H-imidazole

methanol

dichloromethane

→

solid

Rendimiento 76.0%

2-{(1R)-1-[(4-Methoxybenzyl)amino]-2-[indol-3-yl]ethyl}-4-phenyl-1H-imidazole

Rendimiento 76.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónthe slurry was then filtered

Procedimiento

2-{(1R)-1-Amino-2-[indol-3-yl]ethyl}-4-pheny-1H-imidazole (36.3 mg, 0.12 mmol) and panisaldehyde (12 μL, 0.1 mmol) in 1 mL of methanol were shaken for about 2 hours at about 22° C. Borohydride resin (76 mg, 2.5 mmol/g, AMBERLITE® IRA400) was then added and the slurry was stirred overnight before addition of dichloromethane (1 mL) and aldehyde Wang resin (31 mg, 3.22 mmol/g, Novabiochem). After about 8 hours of stirring, the slurry was then filtered and vaporated in vacuo to give a yellow solid (32.2 mg, 76%). 1H-NMR (CDCl3, 100 MHz) δ: 8.86 (br s, 1H); 7.73-6.68 (m, 15H); 4.62 (s, 1H); 4.33 (dd, J=4.7 and 8.5 Hz, 1H); 3.81 (s, 2H); 3.74 (s, 3H); 3.27 (ABX system, 2H); 2.26 (s, 1H). LC/MS: m/z=423 (M+H).

Fuente