反応 #1747828

反応方程式

NaBH3CN

KBr

NaHCO3

acetic acid

hydrochloride

3-(1-Propyl-1,4,5,6-tetrahydro-pyridin-3-yl)-cyclohex-2-enone

→

3-(1-Propyl-piperidin-3-yl)-cyclohex-2-enone

溶媒

water

THF

反応条件

後処理

1. 1
   温度maintaining the temperature
2. 2
   workup.ADDITIONAfter the addition
3. 3
   その他at rt
4. 4
   その他overnight
5. 5
   抽出followed by extraction with dichloromethane (5×50 mL)
6. 6
   乾燥The combined organic layers were dried (MgSO4)
7. 7
   その他evaporated
8. 8
   その他The residue was purified by column chromatography (silica, dichloromethane/ethanol 20:1)
9. 9
   その他to give a colorless oil which
10. 10
    その他Recrystallisation from isoprylether
11. 11
    その他gave 4.2 g, 17.5 mmol (77%), mp 184-185° C

実験手順

3-(1-Propyl-1,4,5,6-tetrahydro-pyridin-3-yl)-cyclohex-2-enone (5.0 g, 22.8 mmol) (from b) above) was dissolved in THF (100 mL). At 0° C., acetic acid (1.38 mL, 22.8 mmol) was added followed by introduction of NaBH3CN (1.9 g, 30.0 mmol) in small portions maintaining the temperature. After the addition was complete the mixture was stirred for 1 h at this temperature and then at rt overnight. Work-up by addition of water (50 mL) and saturated aqueous NaHCO3 (50 mL) followed by extraction with dichloromethane (5×50 mL). The combined organic layers were dried (MgSO4) and evaporated. The residue was purified by column chromatography (silica, dichloromethane/ethanol 20:1) to give a colorless oil which was converted to the hydrochloride. Recrystallisation from isoprylether gave 4.2 g, 17.5 mmol (77%), mp 184-185° C. IR (KBr) 3396, 2941, 2469, 1667, 1455 cm−1; 1H-NMR (CDCl3) δ 5.83 (s, 1H), 3.85 (d, 2H), 2.29-2.56 (m, 7H), 1.23-2.17 (m, 10H), 0.88 (t, 3H) ppm; 13C-NMR (CDCl3) δ 198.4, 165.1, 123.4, 59.0, 55.6, 51.9, 41.6, 36.0, 27.3, 26.9, 22.8, 21.2, 17.6, 10.2 ppm; MS (EI) m/z 221 (M+).

出典