Reaktion #50038

Reaktionsgleichung

Carbobenzyloxy-L-proline

phosphate

ether

→

carbobenzyloxy-L-prolinol

Ausbeute 113.6%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITat ambient temperature for 16 hr
2. 2
   workup.ADDITIONmixed well
3. 3
   SonstigeThe layers were separated
4. 4
   Extraktionthe aqueous portion was extracted with ether (500 mL)
5. 5
   WaschenThe combined organic layers were washed with brine (500 mL)
6. 6
   Trocknendried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   SonstigeThe solvents were evaporated in vacuo

Vorschrift

To Carbobenzyloxy-L-proline (Aldrich, 9.80 g, 39.3 mmol) in THF (100 mL) at 0° C. was added BH3 -THF complex (Aldrich, 1M in THF, 100 mL, 100 mmol). The mixture was stirred at 0° C. for 2 hours, then at ambient temperature for 16 hr. The reaction mixture was poured into pH 7 phosphate buffer solution (500 mL) and ether (600 mL) and mixed well. The layers were separated and the aqueous portion was extracted with ether (500 mL). The combined organic layers were washed with brine (500 mL), dried (Na2SO4) and filtered. The solvents were evaporated in vacuo leaving the crude carbobenzyloxy-L-prolinol as an oil (10.5 g).

Quelle