반응 #1446542

반응 방정식

2-benzyl-3-iodo-6-(3,3-ethylenedioxypyrrolidine-1-yl)pyridine

(3R)-3-ethynyl-3-quinuclidinol

triethylamine

→

target compound

수율 88.5%

(3R)-3-[2-Benzyl-6-(3,3-ethylenedioxypyrrolidine-1-yl]-3-pyridyl]ethynyl-3-quinuclidinol

수율 88.5%

용매

methanol

반응 조건

후처리

1. 1
   기타The reaction solution was partitioned between aqueous dilute ammonia-ethyl acetate
2. 2
   세척washed
3. 3
   세척with washed with water
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   농축concentrated
6. 6
   workup.ADDITION10 ml of tetrahydrofuran was added to the residue
7. 7
   workup.DISSOLUTIONto dissolve
8. 8
   온도under heating
9. 9
   workup.ADDITIONto the mixture was added 15 ml of ethyl acetate
10. 10
    여과The mixture was filtered through 10 g of NH-silica gel
11. 11
    세척washed with ethyl acetate
12. 12
    농축concentrated
13. 13
    기타The residue was crystallized from ethyl acetate

실험 절차

A mixture of 3.0 g of 2-benzyl-3-iodo-6-(3,3-ethylenedioxypyrrolidine-1-yl)pyridine, 1.07 g of (3R)-3-ethynyl-3-quinuclidinol, 82 mg of tetrakis(triphenylphosphine)palladium (0), 68 mg of cuprous iodide, 2.0 ml of triethylamine and 7 ml of methanol was stirred at room temperature overnight in a nitrogen atmosphere. The reaction solution was partitioned between aqueous dilute ammonia-ethyl acetate, washed with washed with water, dried over anhydrous magnesium sulfate and then concentrated. 10 ml of tetrahydrofuran was added to the residue to dissolve under heating, and to the mixture was added 15 ml of ethyl acetate. The mixture was filtered through 10 g of NH-silica gel, washed with ethyl acetate, and concentrated. The residue was crystallized from ethyl acetate, to give 2.79 g of the target compound.

출처