Reacción #42729

Ecuación de reacción

Imidazole

tert-butyldimethylsilyl chloride

(R)-2-Bromo-1-(3-formamido-4-benzyloxyphenyl)ethanol

imidazole

tert-butyldimethylsilyl chloride

→

title compound

Rendimiento 68.0%

N-{2-Benzyloxy-5-[(R)-2-bromo-1-(tert-butyldimethylsilanyloxy)ethyl]phenyl}-formamide

Rendimiento 68.0%

Disolventes

dimethylformamide

—

hexanes

isopropyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction was stirred for an additional 20 h
2. 2
   Otrotransferred to a separatory funnel
3. 3
   LavadoThe organic layer was washed twice with a mixture of water (27 mL) and saturated aqueous sodium chloride (27 mL)
4. 4
   Lavadoa final wash with saturated aqueous sodium chloride (27 mL)
5. 5
   SecadoThe organic layer was dried over sodium sulfate
6. 6
   workup.ADDITIONSilica gel (23.6 g) and hexanes (27 mL) were added
7. 7
   workup.STIRRINGthe suspension was stirred for 10 min
8. 8
   OtroThe solids were removed by filtration
9. 9
   Concentraciónthe filtrate concentrated under vacuum
10. 10
    OtroThe residue was crystallized from hexanes (45 mL)

Procedimiento

(R)-2-Bromo-1-(3-formamido-4-benzyloxyphenyl)ethanol (9.9 g, 28 mmol) was dissolved in dimethylformamide (36 mL). Imidazole (2.3 g, 34 mmol) and tert-butyldimethylsilyl chloride (4.7 g, 31 mmol) were added. The solution was stirred under nitrogen atmosphere for 72 h. Additional imidazole (0.39 g, 5.7 mmol) and tert-butyldimethylsilyl chloride (0.64 g, 4.3 mmol) were added and the reaction was stirred for an additional 20 h. The reaction mixture was then diluted with a mixture of isopropyl acetate (53 mL) and hexanes (27 mL) and transferred to a separatory funnel. The organic layer was washed twice with a mixture of water (27 mL) and saturated aqueous sodium chloride (27 mL) followed by a final wash with saturated aqueous sodium chloride (27 mL). The organic layer was dried over sodium sulfate. Silica gel (23.6 g) and hexanes (27 mL) were added and the suspension was stirred for 10 min. The solids were removed by filtration and the filtrate concentrated under vacuum. The residue was crystallized from hexanes (45 mL) to afford 8.85 g (19 mmol, 68%) of the title compound as a solid. MS m/z: [M+H+] calcd for C22H30NO3SiBr 464.1; found 464.2.

Fuente