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

HRID 1359292

Reaktionsgleichung

Reaktionsgleichung von HRID 1359292
[H-].[Na+].[CH2:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[CH2:20][C@@H:19]([OH:21])[C@H:18]([OH:22])[CH2:17]2)[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:23]I>O1CCCC1>[CH2:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[CH2:17][C@@H:18]([O:22][CH3:23])[C@H:19]([OH:21])[CH2:20]2)[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 693610072-Benzyl-6-[(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]pyridine

Produkt 1

HCID 111968722-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. stirringby stirring as it
  2. stirringby stirring as it
  3. waitwas overnight
  4. extractionThe mixture was extracted with ethyl acetate-water
  5. washthe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. washeluted with 30% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-9379879dfd004c228923b35531334951
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599917B1

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