反応 #360369

反応方程式

(R)-4-butylpyrrolidin-2-one

sodium hydride

5-benzyloxypentyl bromide

→

(R)-1-(5-benzyloxypentyl)-4-butylpyrrolidin-2-one

収率 95.0%

溶媒

dimethylformamide

ethyl acetate

反応条件

後処理

1. 1
   その他at 0° C
2. 2
   workup.STIRRINGThe resulting mixture was stirred at room temperature overnight
3. 3
   洗浄The organic solution was washed with water (4×30 mL) and brine (30 mL)
4. 4
   乾燥dried (Na2SO4)
5. 5
   濃縮concentrated
6. 6
   その他The residue was purified by flash column chromatography (silica gel, 1:1 EtOAc/hexanes)

実験手順

To a solution of (R)-4-butylpyrrolidin-2-one (0.42 g, 2.9 mmol) in dry dimethylformamide (10 mL) under argon was slowly added sodium hydride (60% in mineral oil, 0.14 g, 3.5 mmol) at 0° C. After stirring at 0° C. for 30 minutes, 5-benzyloxypentyl bromide (0.9 g, 3.5 mmol) was added dropwise. The resulting mixture was stirred at room temperature overnight and then diluted with ethyl acetate (50 mL). The organic solution was washed with water (4×30 mL) and brine (30 mL), dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (silica gel, 1:1 EtOAc/hexanes) to afford 0.73 g (95%) of (R)-1-(5-benzyloxypentyl)-4-butylpyrrolidin-2-one as a colorless oil: 1H NMR (CDCl3) δ 7.33 (m, 5 H), 4.51 (s, 2 H), 3.45 (m, 3 H), 3.27 (t, 2 H), 2.99 (dd, 1 H), 2.52 (dd, 1 H), 2.32 (m, 1 H), 2.06 (m, 1 H), 1.24-1.71 (m, 12 H), 0.93 (t, 3 H). MS(ES) m/e 318 [M+H]+.

出典