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

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).

1. customInto a 100-mL round-bottom flask, was placed
2. concentrationThen the mixture was concentrated to dryness under vacuum
3. stirringThe resulting solution was stirred for 30 min at 85° C
4. filtrationThe solid was collected by filtration
5. washwashed with acetone
6. dissolutiondissolved in dichloromethane
7. customTwo phases were separated
8. extractionThe aqueous phase was extracted with dichloromethane
9. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
10. filtrationFiltration and concentration

ORD record

ord-23e9e622abca4cb69d5fb8b8c5ad7d0f

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221809B2