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

HRID 2216341

Reaktionsgleichung

Reaktionsgleichung von HRID 2216341
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][C@@H:17]([OH:19])[C@H:16]([OH:20])[CH2:15]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23]I>O1CCCC1>[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:15][C@@H:16]([O:20][CH3:23])[C@H:17]([OH:19])[CH2:18]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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

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.

Aufarbeitung

  1. stirringthe mixture was stirred as it
  2. extractionThe reaction mixture was extracted with ethyl acetate-water
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-550238ccc6574b4db567877ea19f3fb8
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112593B2

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