N,N,N',N'-Tetramethylethylenediamine → HCID 9905607, compound

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Reaction Steps

To a 1.53M solution of n-butyl lithium in hexane (13.2 mL, 20.2 mmol) was added TMEDA (3.1 mL, 20.2 mmol) under argon atmosphere at room temperature with stirring. To this was added with ice cooling a solution of 5-ethyl-1-indanone(3.24 g, 20.2 mmol) in anhydrous THF followed by stirring at room temperature for 1 hour. After ice cooling the mixture, a solution of 1-ethyl-6-isopropylisatoic anhydride (Example 6, step 1) (2.35 g, 10.1 mmol) in anhydrous THF was added dropwise thereto. The mixture was stirred at room temperature overnight and diluted with saturated aqueous solution of ammonium chloride. The orgaic layer was separated and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with saturated sodium chloride solution and dried with sodium sulfate. After removing the solvent, the residue was purified by silica gel-chromatography (chloroform:acetone=20:1) and crystallization from diethyl ether to give the desired compound. 1H-NMR(CDCl3) δ 1.32(3H,t,CH2CH3), 1.34(6H,d,CH(CH3)2), 1.70(3H,t,NCH2CH3), 2.78(2H,q,CH2CH3), 3.10(1H,septet,CH), 3.91(2H,s,H-11), 4.72(2H,q,NCH2), 7.30-7.85(5H,m,Ar-H), 8.45(1H,s,H-9)

Provenance & Evidence