Reacción #1605826

Ecuación de reacción

ammonium chloride

sodium hydride

di-tert-butyl iminodicarboxylate

1,8-dibromooctane

→

tert-butyl N-(8-bromooctyl)-N-[(tert-butoxy)carbonyl]carbamate

Rendimiento 69.5%

Disolventes

N,N-dimethylformamide

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred for 16 hours
2. 2
   Otroto return to room temperature
3. 3
   Otrothe reaction
4. 4
   Extracciónthe mixture was extracted with ethyl acetate
5. 5
   LavadoThe organic layer was washed with a saturated aqueous solution of sodium chloride
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroThe residue was purified by flash column chromatography

Procedimiento

Under a nitrogen flow, sodium hydride (40% of mineral oil added; 935 mg, 17 mmol) was suspended in N,N-dimethylformamide (160 mL) and, under ice-water cooling, di-tert-butyl iminodicarboxylate (3.26 g, 15 mmol) was added. After stirring under ice-water cooling for 1 hour, a solution of 1,8-dibromooctane (8.16 g, 30 mmol) in N,N-dimethylformamide (10 mL) was added and the mixture was stirred for 16 hours while allowing the mixture to return to room temperature. Under ice-water cooling, a saturated aqueous solution of ammonium chloride was added to stop the reaction and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain tert-butyl N-(8-bromooctyl)-N-[(tert-butoxy)carbonyl]carbamate (4.26 g).

Fuente