Reaction #340316

Reaction equation

(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

Solvents

THF

Conditions

Workup

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

Procedure

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