Reaktion #2303523

Reaktionsgleichung

sodium hydride

2-benzyl-6-[(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]pyridine

methyl iodide

→

title compound

2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridine

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred as it
2. 2
   ExtraktionThe reaction mixture was extracted with ethyl acetate-water
3. 3
   Waschenthe organic layer was washed with water and brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

Vorschrift

To a mixture of 5.35 g of 2-benzyl-6-[(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]pyridine and 40 ml of tetrahydrofuran was added dropwise 800 mg of oily (60%) sodium hydride gradually under stirring, and the mixture was stirred as it was for 1 hour. Then, 1.24 ml of methyl iodide was added thereto and the resultant mixture was stirred overnight as it was. The reaction mixture was extracted with ethyl acetate-water, and the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane), to give 2.18 g of the title compound.

Quelle