(R)-2-Amino-2-ethylhexanoic acid → (R)-2-Amino-2-ethylhexan-1-OL

The product (20 g) from step (e) was added to a 1M solution of lithium aluminum hydride (1.5 molar equivalents) in THF and the mixture was refluxed for 3 hours, then stirred for 16 hours at room temperature. The mixture was cooled to about 0° C., then quenched with water and 1N aqueous NaOH. The resulting solid was broken up with additional water and the suspension was heated at 50° C. for 5 minutes, then cooled to room temperature. Diethyl ether (100 ml) was added, the mixture was stirred and filtered. The diethyl ether layer was separated, dried and concentrated in vacuo to give the desired product as an oil (82% yield), 1H NMR consistent with the proposed structure.

1. temperaturethe mixture was refluxed for 3 hours
2. temperatureThe mixture was cooled to about 0° C.
3. customquenched with water and 1N aqueous NaOH
4. temperaturethe suspension was heated at 50° C. for 5 minutes
5. temperaturecooled to room temperature
6. additionDiethyl ether (100 ml) was added
7. stirringthe mixture was stirred
8. filtrationfiltered
9. customThe diethyl ether layer was separated
10. customdried
11. concentrationconcentrated in vacuo

ORD record

ord-6c280a1c793747dcb5850f2a75df93b1

Source dataset

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05910494