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

(1RS,2SR)-2-(1,3-Dioxo-2-azaindane-2-yl)-4-methyl-1-phenylpentane-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 and, after cooled, ice-cooled and added with 4N hydrochloric acid (700 ml). The mixture was stirred at room temperature for 30 minutes. Insoluble matter was removed by filtration through cellite 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 sodium hydroxide 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 intended compound as white crystals (yield: 91%).

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

ORD record

ord-35e97a730f2b4c3fb81150efce80bb3b

Source dataset

uspto-grants-1987_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04644063