Reaktion #360369

Reaktionsgleichung

(R)-4-butylpyrrolidin-2-one

sodium hydride

5-benzyloxypentyl bromide

→

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

Ausbeute 95.0%

Lösungsmittel

dimethylformamide

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat 0° C
2. 2
   workup.STIRRINGThe resulting mixture was stirred at room temperature overnight
3. 3
   WaschenThe organic solution was washed with water (4×30 mL) and brine (30 mL)
4. 4
   Trocknendried (Na2SO4)
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by flash column chromatography (silica gel, 1:1 EtOAc/hexanes)

Vorschrift

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]+.

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