반응 #47026

반응 방정식

intermediate 76

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

4-fluorobenzylamine

→

product 193

수율 98.1%

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

수율 98.1%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타(reaction block) overnight
2. 2
   온도The reaction mixture is cooled to RT
3. 3
   세척washed with 0.1N HCl, and brine
4. 4
   기타The solvent is evaporated
5. 5
   기타the residue triturated with EtOAc
6. 6
   여과the insoluble material filtered

실험 절차

A mixture of intermediate 76 (200 mg, 0.0.740 mmol), 4-fluorobenzylamine (0.5 mL, 4.4 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 252 mg of the product 193. 1H NMR (CDCl3) δ 8.55 (s, 1 H), 7.55-7.35 (m, 2 H), 7.10-7.00 (m, 2 H), 5.10-4.90 (m, 2 H), 4.30-4.10 (m, 2 H), 2.70-2.55 (m, 1 H), 2.20-2.05 (m, 1 H), 1.80-1.05 (m, 15 H); MS: m/z 348 (M++1)

출처