Реакция #487569

Уравнение реакции

(3R,4R)-1-benzyl-N,4-dimethylpiperidin-3-amine

4-chloro-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine

tri-tert-butylphosphine

sodium tert-butoxide

→

orange oil

Выход 120.8%

N-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]-N-methyl-1-[2-(trimethylsilyl)-ethoxy]methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine

Выход 120.8%

Растворители

toluene

toluene

water

ethyl acetate

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added
2. 2
   ФильтрацияThe resulting suspension was filtered
3. 3
   ДругоеThe aqueous phase was removed
4. 4
   Промывкаthe remaining organic phase was washed with sat. NaCl
5. 5
   Другоеdried
6. 6
   Концентрированиеconcentrated under vacuum

Методика

A degassed mixture of (3R,4R)-1-benzyl-N,4-dimethylpiperidin-3-amine (0.210 g, 0.000962 mol), 4-chloro-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine (0.29 g, 0.0010 mol), tris(dibenzylideneacetone)dipalladium(0) (0.088 g, 0.000096 mol), 0.049 M of tri-tert-butylphosphine in toluene (1.0 mL) and sodium tert-butoxide (0.139 g, 0.00144 mol) in toluene (3 mL, 0.03 mol) was heated to 70° C. for 5 h. After the reaction mixture was cooled to room temperature (rt), ethyl acetate and water were added. The resulting suspension was filtered. The aqueous phase was removed and the remaining organic phase was washed with sat. NaCl, dried, and concentrated under vacuum to give 540 mg orange oil. The crude product was chromatographed using 35% ethyl acetate/hex to give 280 mg orange oil (˜1:1 of two isomers). The mixture was chromatographed again with 35% ethyl acetate/hex several times to separate 44 mg of the higher Rf material.

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