[CH:1]([N:5]1[CH2:8][CH:7]([OH:9])[CH2:6]1)([CH2:3][CH3:4])[CH3:2].[C:10]1([OH:20])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>>[C:10]1([O:20][CH2:6][CH:7]([OH:9])[CH2:8][NH:5][CH:1]([CH2:3][CH3:4])[CH3:2])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1To a mixture of 14.2 parts of 1-(sec.-butyl)-3-azetidinol and 14.4 parts of α-naphthol 0.2 part of sodium hydroxide was added and the mixture was heated under nitrogen gas at 160° C. for 22 hours. The reaction mixture was cooled and then extracted with ether. The extract was washed with 2 N-NaOH aqueous solution and then with water. The liquid was dried over anhydrous sodium sulfate and the solvent was distilled off. Recrystallization of the residue gave 15.5 parts of 1-(α-naphthoxy)-3-(sec.-butylamino)-2-propanol melting at 57°-59° C. The yield was 57%.
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