Réaction #47013

Équation de réaction

intermediate 59

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

3-fluorobenzylamine

→

product 87

Rendement 62.1%

2-(3-Fluorobenzylamino)-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester

Rendement 62.1%

Solvants

MeOH

Conditions de réaction

Traitement

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

Mode opératoire

A mixture of intermediate 59 (2.0 g, 5.42 mmol), 3-fluorobenzylamine (1.86 mL, 16.2 mmol) and MeOH (0.5 mL) is heated at 100° C. for 2 days. The reaction mixture is cooled to RT, and is purified twice by chromatography on silica gel; gradient elution with heptane:EtOAc (70:30-60:40) gives 1.5 g of the product 87. 1H NMR (CDCl3) δ 7.50 (s, 1 H), 7.40-7.30 (m, 1 H), 7.30-7.15 (m, 2 H), 7.10-6.90 (m, 9 H), 7.85-7.75 (m, 2 H), 5.50-5.30 (m, 2 H), 4.80-4.55 (m, 2 H), 1.15 (s, 9 H); MS: m/z 446 (M++1).

Source