Dimethylformamide → (5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol

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Reaction Steps

2-amino-2-(hydroxymethyl)propane-1,3-diol hydrochloride (320 g, 2.03 mol), 2,2-dimethoxypropane (240 g, 2.30 mol), and p-toluenesulfonic acid monohydrate (16.2 g, 102 mmol) were combined into anhydrous dimethylformamide (1.0 L). The solution was stirred vigorously by a mechanical stirrer for 48 hours at room temperature. Triethyl amine (300 mL) and ethyl acetate (1.5 L) were added. A white precipitate formed immediately. The white salt was filtered off and the low boiling point solvents were removed by a rotary evaporator. The product, (5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol, was obtained by distillation (250 g, 76%), by 107° C./0.3 torr. 1H NMR (300 MHz, CDCl3) δ1.48 (s, 3H), 1.53 (s, 3H), 3.14 (br, 2H), 3.51 (s, 1H), 3.53 (d, 2H), 3.78 (d, 2H).

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