Reaktion #1446537

Reaktionsgleichung

2-benzyl-6-[(3R,4R)-3,4-ethylenedioxypyrrolidine-1-yl]-3-iodopyridine

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

triethylamine

ammonia

→

target compound

Ausbeute 66.6%

(3R)-3-[2-Benzyl-6-[(3R,4R)-3,4-ethylenedioxypyrrolidine-1-yl]-3-pyridyl]ethynyl-3-quinuclidinol

Ausbeute 66.6%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with ethyl acetate/tetrahydrofuran (1:1)
2. 2
   WaschenThen, the organic phase was washed with brine
3. 3
   Sonstigethe solvent was removed
4. 4
   SonstigeThe residue was crystallized from tetrahydrofuran/methanol/ethyl acetate

Vorschrift

A mixture of 5.12 g of 2-benzyl-6-[(3R,4R)-3,4-ethylenedioxypyrrolidine-1-yl]-3-iodopyridine, 1.83 g of (3R)-3-ethynyl-3-quinuclidinol, 140 mg of tetrakis(triphenylphosphine)palladium(0), 115 mg of cuprous iodide, 3.4 ml of triethylamine and 12 ml of methanol was stirred at room temperature overnight in a nitrogen atmosphere. The reaction solution was poured into aqueous dilute ammonia, and the mixture was extracted with ethyl acetate/tetrahydrofuran (1:1). Then, the organic phase was washed with brine and the solvent was removed. The residue was crystallized from tetrahydrofuran/methanol/ethyl acetate, to give 3.59 g of the target compound.

Quelle