Reacción #1121726

Ecuación de reacción

linoleyl methanesulfonate

1-(tert-butyldimethylsilyloxy)-3-(dimethylamino)propan-2-ol

NaH

→

3-(tert-butyldimethylsilyloxy)-N,N-dimethyl-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-amine

Rendimiento 53.0%

Disolventes

toluene

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction was then stirred for 18 hours at 90° C
2. 2
   Otroquenched by the slow addition of ethanol (10 mL)
3. 3
   ConcentraciónThe mixture was then concentrated
4. 4
   Extracciónextracted three times with EtOAc (20 mL)
5. 5
   LavadoThe combined organic extracts were washed with deionized water (15 mL)
6. 6
   Secadodried (MgSO4)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated
9. 9
   OtroChromatographic purification of the residue (0-5% MeOH in chloroform)

Procedimiento

A toluene (10 mL) solution of crude 1-(tert-butyldimethylsilyloxy)-3-(dimethylamino)propan-2-ol (1.0 g, 4.29 mmol, 1.0 equiv) was carefully added dropwise to a toluene suspension (5 mL) of NaH (60%, 0.17 g, 4.29 mmol, 1.0 equiv) at 0° C. under argon and the resultant was stirred for 15 minutes. A toluene solution (5 mL) of linoleyl methanesulfonate (1.47 g, 4.29 mmol, 1.0 equiv) was added dropwise to the stirring mixture and the reaction was then stirred for 18 hours at 90° C. The mixture was then cooled to room temperature and quenched by the slow addition of ethanol (10 mL). The mixture was then concentrated and the residue was taken up with deionized water (15 mL) and extracted three times with EtOAc (20 mL). The combined organic extracts were washed with deionized water (15 mL), dried (MgSO4), filtered, and concentrated. Chromatographic purification of the residue (0-5% MeOH in chloroform) yielded 109 mg (53% yield) of 3-(tert-butyldimethylsilyloxy)-N,N-dimethyl-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-amine, a thick clear oil.

Fuente