Reaktion #340316

Reaktionsgleichung

(R)-benzyl 1-oxo-1-phenylpent-4-en-2-ylcarbamate

lithium tri-sec-butylborohydride

→

Benzyl (1R,2R)-1-hydroxy-1-phenylpent-4-en-2-ylcarbamate

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeQuenched
2. 2
   Sonstigethe reaction with saturated aqueous Rochelle's salt (50 mL)
3. 3
   Sonstigethe volatiles were removed in vacuo
4. 4
   ExtraktionThe aqueous residue was extracted with ether (3×50 mL)
5. 5
   Waschenwashed with brine (20 mL)
6. 6
   Trocknendried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   SonstigeThe filtrate was evaporated onto silica gel
9. 9
   Sonstigepurified via flash chromatography (0% to 20%; EtOAc in hexanes)

Vorschrift

To (R)-benzyl 1-oxo-1-phenylpent-4-en-2-ylcarbamate (2.13 g, 6.89 mmol) in THF (50 mL) at −78° C. under argon was added lithium tri-sec-butylborohydride (20.7 ml, 20.7 mmol). Allowed the mixture to stir for 45 min. Quenched the reaction with saturated aqueous Rochelle's salt (50 mL) and the volatiles were removed in vacuo. The aqueous residue was extracted with ether (3×50 mL). The ether was combined and washed with brine (20 mL), dried over Na2SO4 and filtered. The filtrate was evaporated onto silica gel and purified via flash chromatography (0% to 20%; EtOAc in hexanes). MS m/z=334 [M+Na]+. Calc'd for C19H21NO3: 311.

Quelle