Hydrochloric Acid → (1S,5S)-5-amino-2,2-dimethylcyclohexanol hydrochloride

To a mixture of 2-((1R,3R)-3-hydroxy-4,4-dimethylcyclohexyl)isoindoline-1,3-dione and 2-((1S,3S)-3-hydroxy-4,4-dimethylcyclohexyl)isoindoline-1,3-dione (1.1 g, 4.02 mmol) in ethanol (50 mL) was added hydrazine hydrate (0.195 mL, 4.02 mmol). The resulting solution was allowed to stir at reflux overnight under a nitrogen atmosphere. The reaction was cooled to ambient temperature and then the pH was adjusted to <2 via addition of concentrated aqueous hydrochloric acid. The precipitate was filtered off, rinsed with ethanol, and then the resulting filtrate was concentrated to 20 mL under reduced pressure. An equal volume of water was added and this mixture was stirred at ambient temperature for 15 min. The solids were filtered off, rinsed with water, and the filtrate was concentrated under reduced pressure to give a solid that was dried in a vacuum oven for a few hours to afford a mixture of (1R,5R)-5-amino-2,2-dimethylcyclohexanol hydrochloride and (1S,5S)-5-amino-2,2-dimethylcyclohexanol hydrochloride (835 mg, 4.65 mmol, 115% yield) that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.87-8.21 (m, 3H), 2.98-3.23 (m, 1H), 2.75-3.02 (m, 1H), 1.49-1.92 (m, 2H), 1.26-1.47 (m, 3H), 0.96-1.16 (m, 1H), 0.48-0.93 (m, 6H)

1. temperatureat reflux overnight under a nitrogen atmosphere
2. filtrationThe precipitate was filtered off
3. washrinsed with ethanol
4. concentrationthe resulting filtrate was concentrated to 20 mL under reduced pressure
5. additionAn equal volume of water was added
6. stirringthis mixture was stirred at ambient temperature for 15 min
7. filtrationThe solids were filtered off
8. washrinsed with water
9. concentrationthe filtrate was concentrated under reduced pressure
10. customto give a solid
11. customthat was dried in a vacuum oven for a few hours
12. customto afford

ORD 기록

ord-0c138a41128b4b40a5de169227f2e13f

출처 데이터셋

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09139534B2