반응 #10440

반응 방정식

5-benzyl-5-azaspiro[2.4]heptane-7-carboxylic acid ethyl ester

methyllithium

→

title compound

수율 54.6%

1-(5-Benzyl-5-azaspiro[2.4]hept-7-yl)ethanone

수율 54.6%

용매

diethyl ether

반응 조건

후처리

1. 1
   기타reaction mixture
2. 2
   기타quenched with saturated aqueous ammonium chloride
3. 3
   workup.ADDITIONThe mixture is poured into a separatory funnel
4. 4
   세척the organic layer is washed with saturated aqueous ammonium chloride, water, and brine
5. 5
   건조The organic layer is then dried with MgSO4
6. 6
   여과filtered
7. 7
   농축the filtrate concentrated
8. 8
   기타The resulting residue is purified via flash column chromatography (1% triethylamine/7% isopropanol/92% CH2Cl2)

실험 절차

A solution (−78° C.) of 5-benzyl-5-azaspiro[2.4]heptane-7-carboxylic acid ethyl ester (Example A1a, 8.15 g, 31.4 mmol) in diethyl ether (200 mL) under a nitrogen atmosphere is treated with methyllithium (1.4 M in diethyl ether, 22.4 mL, 31.4 mmol) over a period of 10 minutes. After 1 hour, reaction mixture is warmed to −10° C. and quenched with saturated aqueous ammonium chloride. The mixture is poured into a separatory funnel and the organic layer is washed with saturated aqueous ammonium chloride, water, and brine. The organic layer is then dried with MgSO4, filtered, and the filtrate concentrated. The resulting residue is purified via flash column chromatography (1% triethylamine/7% isopropanol/92% CH2Cl2) to afford the title compound (3.93 g). MS CI: m/z 230 (MH+).

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