Reaktion #1446474

Reaktionsgleichung

sodium hydride

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

methyl iodide

→

target compound

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

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGby stirring as it
2. 2
   workup.STIRRINGby stirring as it
3. 3
   workup.WAITwas overnight
4. 4
   ExtraktionThe mixture was extracted with ethyl acetate-water
5. 5
   Waschenthe organic phase was washed with water and brine
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Sonstigeevaporated
8. 8
   Wascheneluted with 30% ethyl acetate/hexane

Vorschrift

800 mg of oily (60%) sodium hydride was added little by little to a mixture of 5.35 g of 2-benzyl-6-[(3R,4R)-3,4-dihydroxypyrrolidine-1-yl]pyridine and 40 ml of tetrahydrofuran while stirring, followed by stirring as it was for one hour. Then 1.24 ml of methyl iodide was added thereto, followed by stirring as it was overnight. The mixture was extracted with ethyl acetate-water, and the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was subjected to silica gel column chromatography and eluted with 30% ethyl acetate/hexane, to give 2.18 g of the target compound.

Quelle