Sodium borohydride → 4-(3-Azidopropoxy)-2,6-dihydroxymethylpyridine

HRID 495882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 495882
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][N:16]=[N+:17]=[N-:18])[CH:9]=[C:8]([C:19](OCC)=[O:20])[N:7]=1)=O)C.[BH4-].[Na+].[Cl-].[Cl-].[Ca+2].[H][H]>ClCCl.C(O)C.O>[N:16]([CH2:15][CH2:14][CH2:13][O:12][C:10]1[CH:11]=[C:6]([CH2:4][OH:3])[N:7]=[C:8]([CH2:19][OH:20])[CH:9]=1)=[N+:17]=[N-:18]

Komponenten

8

Edukt 4

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 22323654Diethyl-4-(3-azidopropoxy)-2,6-pyridinedicarboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 543426824-(3-Azidopropoxy)-2,6-dihydroxymethylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of Diethyl-4-(3-azidopropoxy)-2,6-pyridinedicarboxylate (4.2 mmol) in dichloromethane (10 mL) and absolute ethanol (15 mL), was added in portions, NaBH4 (4.2 mmol) at 25° C. Powdered CaCl2 (4.2 mmol) was added cautiously in small portions and the evolution of hydrogen was allowed to cease before each further addition. The reaction mixture was stirred for 2 hours. Water (100 mL) was added and the reaction mixture was extracted several times with ethyl acetate. The ethyl acetate layers were combined, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by silica gel flash column chromatography to give the title compound. 1H NMR (DMSO) δ 2.00 (m, 2H, CH2), 3.52 (t, 2H, CH2), 4.13 (t, 2H, CH2), 4.45 (d, 4H, 2x CH2), 5.36 (t, 2H, 2x OH), 6.87 (s, 2H, 2x AR).

Aufarbeitung

  1. additionto cease before each further addition
  2. extractionthe reaction mixture was extracted several times with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-58c43f52d21643d69d63c0a7a2892a99
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06942966B1

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