[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([CH:8]([CH3:10])[CH3:9])[C@H:4]([O:11][CH2:12][CH2:13][N:14]([CH2:16][CH2:17][OH:18])[CH3:15])[CH2:3]1.[H-].[Na+].[CH2:21](Br)[CH3:22].O>O1CCCC1>[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([CH:8]([CH3:9])[CH3:10])[C@H:4]([O:11][CH2:12][CH2:13][N:14]([CH2:16][CH2:17][O:18][CH2:21][CH3:22])[CH3:15])[CH2:3]12.57 g of N-[2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)ethyl]-N-(2-hyd roxyethyl)-N-methylamine were dissolved in 100 ml of tetrahydrofuran. 0.48 g of a 50% strength sodium hydride dispersion was added at room temperature, and the reaction mixture was heated under reflux for 3 hours. A solution of 1.1 g of ethyl bromide in 20 ml of tetrahydrofuran was then added dropwise to the reaction solution at boiling temperature, and the reaction solution was heated under reflux for a further 6 hours. The reaction solution was worked up by adding 2 ml of water and concentrating the mixture under reduced pressure. The remaining residue was purified by chromatography on silica gel using n-hexane/dichloromethane/methanol as the eluent. 0.55 g of oily N-[2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)ethyl]-N-(2-etho xyethyl)-N-methylamine was obtained. [α]D20 =-51.20° (c=1; methanol)
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