Réaction #47016

Équation de réaction

intermediate 59

cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-imidazole-1-carboxylic acid, tert-butyl ester

2-fluorophenethylamine

→

product 91

Rendement 43.2%

2-[2-(2-Fluorophenyl)ethylamino]-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester

Rendement 43.2%

Solvants

MeOH

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture is cooled to RT
2. 2
   Autreis purified by chromatography on silica gel
3. 3
   Lavagegradient elution with heptane:EtOAc (70:30-60:40)

Mode opératoire

A mixture of intermediate 59 (0.5 g, 1.36 mmol), 2-fluorophenethylamine (0.531 mL, 4.07 mmol) and MeOH (0.1 mL) is heated at 100° C. for 3 days. The reaction mixture is cooled to RT, and is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (70:30-60:40) gives 0.27 g of the product 91. 1H NMR (CDCl3) δ 7.40-6.85 (m, 13 H), 6.80-6.65 (m, 2 H), 5.45-5.25 (m, 2 H), 3.90-3.60 (m, 2 H), 1.15 (s, 9 H); MS: m/z 460 (M++1).

Source