反応 #5445

反応方程式

product

8-Methoxy-2-(2-aminoethyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

p-fluorobenzoyl chloride

→

desired product

8-Methoxy-2-(2-(4-fluorobenzamido)ethyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole hydrochloride

溶媒

triethyl amine

methylene chloride

反応条件

後処理

1. 1
   その他the reaction was quenched in 5% NaHCO3
2. 2
   抽出extracted with ethyl acetate
3. 3
   乾燥The organic extracts were dried (Na2SO4)
4. 4
   その他evaporated
5. 5
   workup.DISSOLUTIONthe product was dissolved in ether
6. 6
   workup.ADDITIONtreated with ethereal HCl
7. 7
   その他evaporated to dryness
8. 8
   その他The resulting product was recrystallized from ethyl acetate and ether

実験手順

The product from Example 17 (0.95 g) was dissolved in 50 ml methylene chloride and 1.5 ml triethyl amine. The solution was cooled to -20° C. and 0.59 ml p-fluorobenzoyl chloride was added. After 30 min, the reaction was quenched in 5% NaHCO3 and extracted with ethyl acetate. The organic extracts were dried (Na2SO4), evaporated, and the product was dissolved in ether and treated with ethereal HCl and then evaporated to dryness. The resulting product was recrystallized from ethyl acetate and ether to yield 0.772 g of the desired product as a white solid, mp: 197°-8° C. NMR (d6DMSO) δ2.60-3.10 (m, 3H), 3.00-3.50 (m, 4H), 3.59 (m, 2H), 3.78 (s, 3H), 3.82-4.22 (m, 3H), 6.83 (d, 1H), 6.87 (d, 1H), 7.23 (t, 1H), 7.34 (m, 2 H), 8.00 (m, 2H).

出典