[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[CH:23]([CH3:27])[C:24](Cl)=[O:25].[OH-].[K+]>ClCCl.CC(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][O:12][CH:23]([CH3:27])[C:24]2=[O:25])=[CH:13][CH:14]=1
To a solution of 3-(4-methoxy-benzylamino)-propan-1-ol (2.00 g, 10.2 mmol) in dichloromethane (30 ml) was added triethylamine (1.09 g, 10.8 mmol) and 2-chloropropionyl chloride (1.37 g, 10.8 mmol) at 0° C. The mixture was stirred at 0° C. for one hour and partitioned between 0.5N hydrochloric acid and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was dissolved into 2-propanol (50 ml) and potassium hydroxide (1.15 g, 20.5 mmol) was added at 0° C. The resulting mixture was stirred at 0° C. for 4 hours and partitioned between saturated ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=3/1) to afford 4-(4-methoxybenzyl)-2-methyl-[1,4]oxazepan-3-one as colorless oil (2.00 g, 78%).
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