Hydrochloric Acid → 1,3-Dioxolane-4-methanamine, 2,2-dimethyl-

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Reaction Steps

Into a 100-mL round-bottom flask, was placed a solution of 3-aminopropane-1,2-diol (5 g, 54.88 mmol, 1.00 equiv) in water (15 mL). The pH value of the solution was adjusted to 1 with 37% hydrochloric acid. The resulting solution was stirred for 15 min at room temperature. Then the mixture was concentrated to dryness under vacuum. This was followed by the addition of 2,2-dimethoxypropane (32 mL), and 4-methylbenzene-1-sulfonic acid (423 mg, 2.46 mmol, 0.04 equiv). The resulting solution was stirred for 30 min at 85° C. The solid was collected by filtration, washed with acetone and then dissolved in dichloromethane. The PH value of the solution was adjusted to 9 with 2N sodium hydroxide solution. Two phases were separated. The aqueous phase was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate. Filtration and concentration under reducing pressure gave the title compound (light yellow oil). 1H-NMR (300 MHz, CDCl3): δ ppm 1.24(s, 3H), 1.33(s, 3H), 2.77 (s, 1H), 2.91(s, 1H), 3.67-3.72(m, 1H), 3.96-4.01(m, 1H), 4.20-4.28(m, 1H), 8.15(brs, 3H).

Provenance & Evidence