Example 29: 2,2,2-Trimethylacetamide (1.0 g, 9.89 mmol) was used as starting material and dissolved in THF (100 mL). Under argon protection, LiAlH4 (2.0 M solution of THF, 14.83 mL, 29.7 mmol) was slowly added and the reaction was stirred at room temperature overnight. Upon completion of the reaction, the reaction was quenched by slow addition of water (1.125 mL), 20% KOH solution (1.125 mL), and water (2.25 mL) in that order, with vigorous stirring for 10 min. Na2SO4 was added to treat the reaction mixture and the solids were removed by diatomaceous earth filtration and the filter pad was washed with THF. The filtrate was treated with a methanol solution of 1M HCl (15 mL) and concentrated to dryness to afford the target product 2,2-dimethylpropan-1-amine hydrochloride (413 mg, 34% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 7.88 (br s, 2H), 2.57 (s, 2H), 0.93 (s, 9H).
