反応 #799616

反応方程式

octahydrocyclopenta[c]pyrrole hydrochloride

K2CO3

1-chloro-3-bromopropane

→

title compound

収率 56.6%

2-(3-chloropropyl)octahydrocyclopenta[c]pyrrole

収率 56.6%

溶媒

acetone

反応条件

後処理

1. 1
   温度The reaction mixture was heated
2. 2
   温度to reflux for 12 h under N2
3. 3
   その他The solvent was removed
4. 4
   workup.ADDITIONthe residue was treated with 200 mL of EtOAc
5. 5
   洗浄The mixture was washed with water
6. 6
   乾燥The mixture was dried over anhydrous Na2SO4
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The residue was chromatographed with a silica gel column (eluting agent: 1:1 (v/v) PE/EtOAc)

実験手順

To a suspension of octahydrocyclopenta[c]pyrrole hydrochloride (5.00 g, 33.86 mmol) in acetone (150 mL) was added K2CO3 (35.68 g, 101.59 mmol) and 1-chloro-3-bromopropane (10.56 g, 67.72 mmol) in turn. The reaction mixture was heated to reflux for 12 h under N2. The solvent was removed, and the residue was treated with 200 mL of EtOAc. The mixture was washed with water followed by brine. The mixture was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 1:1 (v/v) PE/EtOAc) to afford the title compound (3.06 g, 56.63%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 188.7 (M+1); 1H NMR (400 MHz, CDCl3) δ: 1.24-1.28 (m, 1H), 1.38-1.40 (m, 2H), 2.06 (m, 1H), 2.46-2.50 (m, 2H), 2.56-2.57 (m, 3H), 2.63-2.68 (m, 2H), 2.70 (d, J=2.24 Hz, 2H), 2.71-2.73 (m, 2H), 3.60 (m, 2H) ppm.

出典