反応 #47011

反応方程式

intermediate 59

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

4-fluorobenzylamine

→

product 85

収率 41.6%

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

収率 41.6%

溶媒

MeOH

反応条件

後処理

1. 1
   温度The reaction mixture is cooled to RT
2. 2
   その他partitioned between dichloromethane and water
3. 3
   その他The organic solution is separated
4. 4
   乾燥dried (MgSO4)
5. 5
   濃縮concentrated in vacuo
6. 6
   その他The residue is purified by chromatography on silica gel
7. 7
   洗浄gradient elution with heptane:EtOAc (80:20-40:60)

実験手順

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).

出典