反応 #1726678

反応方程式

hydrochloric acid

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

NaOH

→

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

溶媒

acetic acid

反応条件

後処理

1. 1
   温度under reflux overnight
2. 2
   抽出the unclear solution was extracted with ethyl acetate (2×40 ml)
3. 3
   乾燥The combined organic phases were dried (MgSO4)
4. 4
   その他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
   その他The target compound was collected as a white oxalic salt
8. 8
   その他RT=2.24

実験手順

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%).

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