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0 °C

A solution of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (1.5 g, 6.1 mmole) in 8 mL THF was treated with 2.5 mL of lithium aluminium hydride solution (1M in THF). The reaction mixture was heated to reflux for 3.5 hours. The mixture was cooled to 0° C. and treated with 0.95 mL water, 0.95 mL 15% aqueous sodium hydroxide solution and 3.0 mL water. The mixture was stirred at room temperature until a white precipitate formed. MgSO4 was added, the mixture was filtered and concentrated in vacuo, giving a pale yellow oil. The product was purified by flash chromatography (SiO2, 15% ethyl acetate/hexanes), yielding 1.2 g (86%) of N-ethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine, as a colourless oil.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 3.5 hours
3. customformed
4. filtrationthe mixture was filtered
5. concentrationconcentrated in vacuo
6. customgiving a pale yellow oil
7. customThe product was purified by flash chromatography (SiO2, 15% ethyl acetate/hexanes)