Réaction #50410

Équation de réaction

n-butyl lithium

hexane

2-tert.butoxycarbonylamino-6-bromo-1,2,3,4-tetrahydro-naphthaline

pyridine-3-aldehyde

→

2-tert.Butoxycarbonylamino-6-bromo-1,2,3,4-tetrahydronaphth-6-yl-3-pyridylmethanol

Solvants

tetrahydrofurane

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGAfter stirring for one hour
2. 2
   workup.ADDITIONthe reaction mixture was poured on ice
3. 3
   Extractionextracted with ethyl acetate
4. 4
   LavageThe organic phase was washed with water
5. 5
   Autredried
6. 6
   Autreevaporated
7. 7
   AutreThe obtained residue was recrystallised from cyclohexane/ethyl acetate

Mode opératoire

8.8 ml of a solution of n-butyl lithium in hexane (2.5 mol) was dropped to a solution of 3.25 g of 2-tert.butoxycarbonylamino-6-bromo-1,2,3,4-tetrahydro-naphthaline in 50 ml of absolute tetrahydrofurane cooled to -70° C. and stirring was continued for 1.5 hours at -50° C. Subsequently, 1.1 g of pyridine-3-aldehyde were dropped into the mixture at -70° C. After stirring for one hour, the reaction mixture was poured on ice and extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated. The obtained residue was recrystallised from cyclohexane/ethyl acetate.

Source