Hydrochloric Acid → (1RS,2SR)-2-Amino-4-methyl-1-phenylpentan-1-ol

(1RS,2SR)2-(1,3-Dioxo-2-azaindan-2-yl)-4-methyl-1-phenylpentan-1-ol (80.0 g, 247 mmol) was dissolved with heating (50° C.) in ethanol (800 ml), followed by addition of a mixture of 85% hydrazine hydrate (19.0 ml) in ethanol (200 ml). The resulting mixture was heated under reflux for 3 hours. After ice-cooling, 4N-HCl (700 ml) was added. The mixture was stirred at room temperature for 30 minutes. Insoluble matter was removed by filtration through celite and then washed with 4N-hydrochloric acid (140 ml). The washing was added to the filtrate and the solution was condensed under reduced pressure to remove the ethanol. A 6N-NaOH solution (570 ml) was added with ice-cooling and the mixture was extracted three times with chloroform. After being dried over sodium sulfate, the organic layer was evaporated to obtain 43.2 g of the title compound as white crystals (yield: 91%).

1. temperatureThe resulting mixture was heated
2. temperatureunder reflux for 3 hours
3. temperatureAfter ice-cooling
4. customInsoluble matter was removed by filtration through celite
5. washwashed with 4N-hydrochloric acid (140 ml)
6. additionThe washing was added to the filtrate
7. customcondensed under reduced pressure
8. customto remove the ethanol
9. additionA 6N-NaOH solution (570 ml) was added with ice-
10. temperaturecooling
11. extractionthe mixture was extracted three times with chloroform
12. dry with materialAfter being dried over sodium sulfate
13. customthe organic layer was evaporated

ORD record

ord-b3de94b8d22146f2b9b5a5919790da3c

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05250546