反应 #1726678

反应方程式

hydrochloric acid

1-tert-butoxycarbonyl-4-[2-(4-methylphenylsulfanyl)phenyl]piperidin-4-ol

NaOH

→

4-[2-(4-Methylphenylsulfanyl)phenyl]-3,6-dihydro-2H-pyridine

溶剂

acetic acid

反应条件

后处理

1. 1
   温度under reflux overnight
2. 2
   萃取the unclear solution was extracted with ethyl acetate (2×40 ml)
3. 3
   干燥The combined organic phases were dried (MgSO4)
4. 4
   其他the solvents evaporated in vacuo
5. 5
   workup.DISSOLUTIONThe crude material (0.48 g) was dissolved in ethyl acetate (3.2 mL) at 50° C.
6. 6
   workup.ADDITIONa solution of oxalic acid (0.11 g) in EtOH (3.2 mL) was slowly added
7. 7
   其他The target compound was collected as a white oxalic salt
8. 8
   其他RT=2.24

实验过程

Concentrated aq hydrochloric acid (10 ml) was added to a stirred solution of 1-tert-butoxycarbonyl-4-[2-(4-methylphenylsulfanyl)phenyl]piperidin-4-ol (0.84 g, 2.1 mmol) in acetic acid (30 mL). The solution was boiled under reflux overnight, cooled to room temperature and then stirred in an ice bath. An aqueous solution of NaOH (9.1 M, 40 mL) was slowly added and the unclear solution was extracted with ethyl acetate (2×40 ml). The combined organic phases were dried (MgSO4) and the solvents evaporated in vacuo. The crude material (0.48 g) was dissolved in ethyl acetate (3.2 mL) at 50° C. and a solution of oxalic acid (0.11 g) in EtOH (3.2 mL) was slowly added. The target compound was collected as a white oxalic salt. 1H (DMSO-d6) δ 7.3-7.2 (m, 7H); 7.15 (m, 1H); 7.00 (m, 1H); 5.6 (d, 1H); 3.7 (d, 2H); 3.25 (t, 2H); 2.6 (m, 2H); 2.3 (s, 3H). LC/MS (m/z) 282.2 (MH+); RT=2.24; purity (UV, ELSD): 99%, 100%; yield: 0.31 g (40%).

来源