Реакция #4352

Уравнение реакции

Boc-leucinal

vinyl magnesium bromide

→

desired product

Выход 65.0%

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

Выход 65.0%

Растворители

tetrahydrofuran

THF

Условия реакции

Обработка

1. 1
   Другоеthe mixture was quenched with 1.0M NH4Cl (50 ml)
2. 2
   ДругоеMost of the THF was evaporated in vacuo
3. 3
   Экстракцияthe residue was extracted with ether several times
4. 4
   ПромывкаThe combined extracts were washed (brine)
5. 5
   Сушкаdried (Na2SO4)
6. 6
   Фильтрацияfiltered
7. 7
   Другоеevaporated

Методика

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.

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