Methyl 2-(piperidin-1-yl)pyridine-4-carboxylate → [2-(Piperidin-1-yl)pyridin-4-yl]methanol

HRID 1174510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1174510
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][N:22]=2)[C:16](OC)=[O:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C1COCC1>[N:7]1([C:13]2[CH:14]=[C:15]([CH2:16][OH:17])[CH:20]=[CH:21][N:22]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Komponenten

4

Edukt 2

HCID 18525843Methyl 2-(piperidin-1-yl)pyridine-4-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 18525842[2-(Piperidin-1-yl)pyridin-4-yl]methanolAusbeute 65,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of LAH (5.5 g, 0.145 mol) in dry THF (500 mL) at 0° C. was added methyl 2-piperidin-1-ylisonicotinate (18 g, 0.095 mol) in dry THF (100 mL) under N2 atmosphere. The reaction mixture was stirred at RT for 4 h and quenched with 10% aqueous NaOH solution at −20° C. The solid was filtered off, washed with THF and concentrated. The residue was dissolved in CH2Cl2 (250 mL), washed with water, brine and dried. The solvent was removed under vacuum and the crude was purified by column chromatography over silica gel (CHCl3/MeOH, 9:1) to give (2-piperidin-1-yl pyridin-4-yl)methanol (12 g, 65%). 1H NMR (DMSO-d6) δ 7.98 (d, J=5.2 Hz, 1H), 6.71 (s, 1H), 6.51 (br d, 1H), 5.24 (t, J=5.2 Hz, 1H), 4.41 (d, J=5.2 Hz, 2H), 3.49-3.46 (m, 4H), 1.58-1.50 (m, 6H).

Aufarbeitung

  1. customquenched with 10% aqueous NaOH solution at −20° C
  2. filtrationThe solid was filtered off
  3. washwashed with THF
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in CH2Cl2 (250 mL)
  6. washwashed with water, brine
  7. customdried
  8. customThe solvent was removed under vacuum
  9. customthe crude was purified by column chromatography over silica gel (CHCl3/MeOH, 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-ef43a2b0866d40839e76d95162fe3c53
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838522B2

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