反応 #49084

反応方程式

Isocyanate

potassium cyanide

2-(RS)-methylpyrrolidine

acetone

→

title compound

収率 37.5%

2-Methyl-2-(2-methyl-1-pyrrolidinyl)propanenitrile

収率 37.5%

溶媒

water

DCM

反応条件

後処理

1. 1
   温度To a stirred, ice-cooled
2. 2
   その他the crude reaction mixture
3. 3
   抽出was extracted with diethyl ether (2×200 ml)
4. 4
   洗浄the combined extracts washed with brine (200 ml)
5. 5
   乾燥dried (Na2SO4)
6. 6
   その他evaporated under reduced pressure
7. 7
   その他to afford a pale yellow oil
8. 8
   workup.STIRRINGThe mixture was stirred for 3 hours
9. 9
   ろ過filtered
10. 10
    その他the filtrate evaporated

実験手順

To a stirred, ice-cooled mixture of 2-(RS)-methylpyrrolidine (4.25 g; 0.05 mol) and acetone (3.67 ml; 0.05 mol) was added a solution of potassium cyanide (3.25 g; 0.05 mol) in water (25 ml) dropwise over 10 min. After stirring at room temperature overnight, the crude reaction mixture was extracted with diethyl ether (2×200 ml) and the combined extracts washed with brine (200 ml), dried (Na2SO4) and evaporated under reduced pressure to afford a pale yellow oil. This was dissolved in DCM and PS-Isocyanate (4.5 g of resin loading 1.53 mmol/g) added. The mixture was stirred for 3 hours, filtered and the filtrate evaporated to afford the title compound as a colourless semi-solid (2.82 g; 37.5%). 1H NMR (CDCl3) δ(inter alia): 1.10 (3H, d), 1.45 (3H, s), 1.55 (3H, s), 1.75-2.00 (4H, m) 2.65 (1H, m) and 3.05-3.20 (2H, m).

出典