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0 °C

To a solution of 6-methoxy-2-naphthaldehyde (3.00 g, 16.1 mmol) and pyrrolidine (2.69 ml, 32.2 mmol) in tetrahydrofuran (32 ml) and acetic acid (16 ml) was added sodium triacetoxyhydroborate. (6.83 g, 32.2 mmol) at 0° C., and the mixture was stirred at room temperature for 7 hours. The solvent was distilled off under reduced pressure, 1N hydrochloric acid was added to the resulting oil, and the mixture was washed with diethyl ether. An 8N aqueous sodium hydroxide solution was added to the aqueous layer, followed by extraction with ethyl acetate. The extract was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to obtain the titled compound (3.89 g).

1. distillationThe solvent was distilled off under reduced pressure, 1N hydrochloric acid
2. additionwas added to the resulting oil
3. washthe mixture was washed with diethyl ether
4. additionAn 8N aqueous sodium hydroxide solution was added to the aqueous layer
5. extractionfollowed by extraction with ethyl acetate
6. washThe extract was washed with an aqueous saturated sodium chloride solution
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationThe solvent was concentrated under reduced pressure