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

HRID 2216342

Reaktionsgleichung

Reaktionsgleichung von HRID 2216342
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][C@@H:17]([O:19][CH3:20])[C@H:16]([OH:21])[CH2:15]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:22]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[CH2:1]([C:8]1[C:13]([I:22])=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][C@@H:17]([O:19][CH3:20])[C@H:16]([OH:21])[CH2:15]2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 24437Sodium SulfiteHCID 120273N-IodosuccinimideHCID 111968722-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridine

Produkt 1

HCID 113843072-Benzyl-3-iodo-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridineAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 3.11 g of 2-benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridine and 10 ml of N,N-dimethylformamide, while stirring in an ice bath, was added dropwise 2.5 g of N-iodosuccinimide, and the resultant mixture was stirred overnight as it was. To this was added sodium sulfite and 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 4.19 g of the title compound.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7f79858587ff48f09b85eedf4ca608c2
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112593B2

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