Reaktion #4352

Reaktionsgleichung

Boc-leucinal

vinyl magnesium bromide

→

desired product

Ausbeute 65.0%

(3RS,4S)-4-t-Butyloxycarbonylamino-3-hydroxy-6-methylhept-1-ene

Ausbeute 65.0%

Lösungsmittel

tetrahydrofuran

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture was quenched with 1.0M NH4Cl (50 ml)
2. 2
   SonstigeMost of the THF was evaporated in vacuo
3. 3
   Extraktionthe residue was extracted with ether several times
4. 4
   WaschenThe combined extracts were washed (brine)
5. 5
   Trocknendried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated

Vorschrift

To a stirred 0° C. solution of Boc-leucinal (3.00 g, 13.9 mmol) in dry tetrahydrofuran (THF) (70 ml) was added vinyl magnesium bromide (35 ml of a 1.0M solution in THF). After 5 hours, the mixture was quenched with 1.0M NH4Cl (50 ml). Most of the THF was evaporated in vacuo and the residue was extracted with ether several times. The combined extracts were washed (brine), dried (Na2SO4), filtered, and evaporated to give the desired product as a 3:2 mixture of hydroxy diastereomers in 65% yield.

Quelle