تفاعل #4352

معادلة التفاعل

Boc-leucinal

vinyl magnesium bromide

→

desired product

المردود 65.0%

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

المردود 65.0%

المذيبات

tetrahydrofuran

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىthe mixture was quenched with 1.0M NH4Cl (50 ml)
2. 2
   أخرىMost of the THF was evaporated in vacuo
3. 3
   استخلاصthe residue was extracted with ether several times
4. 4
   غسيلThe combined extracts were washed (brine)
5. 5
   تجفيفdried (Na2SO4)
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated

الإجراء التجريبي

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.

المصدر