Réaction #340316

Équation de réaction

(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

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreQuenched
2. 2
   Autrethe reaction with saturated aqueous Rochelle's salt (50 mL)
3. 3
   Autrethe volatiles were removed in vacuo
4. 4
   ExtractionThe aqueous residue was extracted with ether (3×50 mL)
5. 5
   Lavagewashed with brine (20 mL)
6. 6
   Séchagedried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   AutreThe filtrate was evaporated onto silica gel
9. 9
   Autrepurified via flash chromatography (0% to 20%; EtOAc in hexanes)

Mode opératoire

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.

Source