[OH:1][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][OH:14])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[OH-].[Na+].Br[CH2:18][CH2:19][CH3:20].C(Cl)Cl.[CH3:24][CH2:25][CH2:26]CCC>O.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[CH2:18]([O:1][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][O:14][CH2:24][CH2:25][CH3:26])[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:19][CH3:20]
To a solution of tert-butyl bis(2-hydroxyethyl)carbamate (8.20 g, 40 mmol) in hexane (30 mL) was added a solution of NaOH (8.00 g, 200 mmol) in water (30 mL), 1-bromopropane (9.84 g, 80 mmol) and TBAB (1.00 g) under N2. The reaction mixture was refluxed overnight, then cooled to rt and poured into CH2Cl2 (100 mL). The organic phase was washed with water (100 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as colorless oil (1.78 g, 15%).
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