Reaktion #47027

Reaktionsgleichung

intermediate 76

cis-3a,4,5,6,7,7a-Hexahydro-2-methylthio-benzimidazole-1-carboxylic acid, tert-butyl ester

3,4-difluorobenzylamine

→

product 195

Ausbeute 99.8%

2-[(3,4-Difluorobenzyl)amino]-cis-3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-1-carboxylic acid tert-butyl ester

Ausbeute 99.8%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(reaction block) overnight
2. 2
   TemperaturThe reaction mixture is cooled to RT
3. 3
   Waschenwashed with 0.1N HCl, and brine
4. 4
   SonstigeThe solvent is evaporated
5. 5
   Sonstigethe residue triturated with EtOAc
6. 6
   Filtrationthe insoluble material filtered

Vorschrift

A mixture of intermediate 76 (200 mg, 0.740 mmol), 3,4-difluorobenzylamine (0.5 mL, 4.2 mmol) is heated at 100° C. (reaction block) overnight. The reaction mixture is cooled to RT. The reaction mixture is diluted with dichloromethane, washed with 0.1N HCl, and brine. The solvent is evaporated, and the residue triturated with EtOAc, and the insoluble material filtered to give 270 mg of the product 195. 1H NMR (CDCl3) δ 8.60 (s, 1 H), 7.40-7.10 (m, 3 H), 5.15-4.90 (m, 2 H), 4.30-4.10 (m, 2 H), 2.70-2.55 (m, 1 H), 2.20-2.05 (m, 1 H), 1.85-1.10 (m, 15 H); MS: m/z 366 (M++1).

Quelle