反応 #47026

反応方程式

intermediate 76

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

4-fluorobenzylamine

→

product 193

収率 98.1%

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

収率 98.1%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他(reaction block) overnight
2. 2
   温度The reaction mixture is cooled to RT
3. 3
   洗浄washed with 0.1N HCl, and brine
4. 4
   その他The solvent is evaporated
5. 5
   その他the residue triturated with EtOAc
6. 6
   ろ過the insoluble material filtered

実験手順

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)

出典