Ammonium Chloride → (R)-2-Hydroxy-2-(3-isoxazolyl)ethylamine

Temperatur

0 °C

To ytterbium(III) chloride in acetonitrile (10 ml) was added 2,6-bis[(4S)-(−)-isopropyl-2-oxazolin-2-yl]pyridine (180 mg) and the solution stirred for 1 h. After cooling to 0° C., 3-isoxazolecarboxaldehyde (580 mg) in acetonitrile (5 ml) followed by TMSCN (0.96 ml) were added. After warming to room temperature overnight, aqueous ammonium chloride solution was added and the product extracted into diethyl ether. The extracts were dried (Na2SO4), the solvent was evaporated off, and the residue taken up in diethyl ether (50 ml). After cooling to 0° C., the solution was added to lithium aluimnium hydride (570 mg) in diethyl ether (10 ml) at 0° C. After 3 h at room temperature, water (0.54 ml), 15% aqueous sodium hydroxide (1.62 ml) and water (0.54 ml) were added sequentially. The mixture was filtered through celite and the solvent was evaporated off to give the sub-title compound as a yellow oil (250 mg, 40% ee).

1. additionwere added
2. temperatureAfter warming to room temperature overnight
3. extractionthe product extracted into diethyl ether
4. dry with materialThe extracts were dried (Na2SO4)
5. customthe solvent was evaporated off
6. temperatureAfter cooling to 0° C.
7. additionthe solution was added to lithium aluimnium hydride (570 mg) in diethyl ether (10 ml) at 0° C
8. waitAfter 3 h at room temperature
9. additionwater (0.54 ml), 15% aqueous sodium hydroxide (1.62 ml) and water (0.54 ml) were added sequentially
10. filtrationThe mixture was filtered through celite
11. customthe solvent was evaporated off

ORD-Eintrag

ord-94cbc1dfed0a4c14823d520b7b76225e

Quelldatensatz

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07223794B2