Reaktion #47005

Reaktionsgleichung

intermediate 59

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

cyclohexanemethylamine

→

product 79

Ausbeute 39.0%

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

Ausbeute 39.0%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is cooled to RT
2. 2
   Sonstigepurified by chromatography on silica gel
3. 3
   Waschengradient elution with heptane:EtOAc (70:30-50:50)

Vorschrift

A mixture of intermediate 59 (0.5 g, 1.36 mmol), cyclohexanemethylamine (0.53 mL, 6.1 mmol) and MeOH (0.11 mL) is heated at 100° C. for 48 h. The reaction mixture is cooled to RT and purified by chromatography on silica gel; gradient elution with heptane:EtOAc (70:30-50:50) gives 0.23 g of the product 79. 1H NMR (CDCl3) δ 7.80-7.35 (m, 2 H), 7.18 9s, 1 H), 7.10-6.90 (m, 6 H), 6.90-6.70 (m, 2 H), 5.45-5.30 (m, 2 H), 3.45-3.15 (m, 2 H), 2.00-1.50 (m, 5 H), 1.45-0.95 (m, 15H); MS: m/z 434 (M++1).

Quelle