Réaction #47011

Équation de réaction

intermediate 59

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

4-fluorobenzylamine

→

product 85

Rendement 41.6%

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

Rendement 41.6%

Solvants

MeOH

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture is cooled to RT
2. 2
   Autrepartitioned between dichloromethane and water
3. 3
   AutreThe organic solution is separated
4. 4
   Séchagedried (MgSO4)
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe residue is purified by chromatography on silica gel
7. 7
   Lavagegradient elution with heptane:EtOAc (80:20-40:60)

Mode opératoire

A mixture of intermediate 59 (1.0 g, 0.0027 mol), 4-fluorobenzylamine (0.372 mL, 0.00321 mol) and MeOH (0.4 mL) is heated at 100° C. for 2 days. The reaction mixture is cooled to RT, and partitioned between dichloromethane and water. The organic solution is separated, dried (MgSO4), and concentrated in vacuo. The residue is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (80:20-40:60) gives 0.50 g of the product 85. 1H NMR (CDCl3) δ 7.60-7.35 (m, 3 H), 7.15-6.90 (m, 10 H), 6.85-6.70 (m, 2 H), 5.50-5.30 (m, 2 H), 5.75-5.55 (m, 2 H), 1.12 (s, 9 H); MS: m/z 446 (M++1).

Source