Sodium Hydroxide → (2R)-2-(Propylamino)pentan-1-OL

Temperature

4 °C

Lithium aluminum hydride (5.47 g) was added to tetrahydrofuran (144 mL) with stirring at 4° C. and then stirred under ice-cooling for 15 minutes. A solution of (R)—N-propionylnorvaline methyl ester (15.87 g) in tetrahydrofuran (85 mL) was added dropwise to the resulting suspension over 70 minutes under stirring at 4° C. and then stirred for 15 minutes under ice-cooling. The suspension was refluxed and stirred for 2 hours and then stirred under ice-cooling for 20 minutes, and an aqueous solution (25 mL) of 1 mol/L sodium hydroxide was added dropwise thereto over 12 minutes and stirred under ice-cooling for 5 minutes. The suspension was refluxed and stirred for 1 hour. The suspension was filtered and washed with ethyl acetate (23 mL). The insoluble matter was subsequently washed twice with hot ethyl acetate (115 mL). The filtrate and the washings were combined and dried over anhydrous sodium sulfate for 12 hours and then concentrated under reduced pressure to give (R)—N-propylnorvalinol (11.97 g, 97% yield) as a yellow oil.

1. stirringstirred under ice-
2. temperaturecooling for 15 minutes
3. stirringunder stirring at 4° C.
4. stirringstirred for 15 minutes under ice-
5. temperaturecooling
6. temperatureThe suspension was refluxed
7. stirringstirred for 2 hours
8. stirringstirred under ice-
9. temperaturecooling for 20 minutes
10. stirringstirred under ice-
11. temperaturecooling for 5 minutes
12. temperatureThe suspension was refluxed
13. stirringstirred for 1 hour
14. filtrationThe suspension was filtered
15. washwashed with ethyl acetate (23 mL)
16. washThe insoluble matter was subsequently washed twice with hot ethyl acetate (115 mL)
17. dry with materialdried over anhydrous sodium sulfate for 12 hours
18. concentrationconcentrated under reduced pressure

ORD record

ord-7a70c5b68a2d4d8eab2a921b6609ec21

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178686B2