Aluminium lithium hydride → 1-Boc-4-(hydroxymethyl)-4-methylpiperidine

HRID 1986177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986177
C[O:2][C:3]([C:5]1([CH3:18])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C:5]([CH2:3][OH:2])([CH3:18])[CH2:6][CH2:7]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 463183881-tert-Butyl 4-methyl 4-methylpiperidine-1,4-dicarboxylate

Produkt 1

HCID 232828431-Boc-4-(hydroxymethyl)-4-methylpiperidineAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-Methylpiperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (1.48 g, 5.73 mmol) is dissolved in THF (15 mL) and cooled to 0° C. 1.0 M lithium aluminum hydride in THF (6.30 mL, 6.30 mmol) is added dropwise. After 1.25 hours the reaction is quenched with MeOH, then stirred with saturated Rochelle's salt until two layers form. The two layers are separated and the aqueous layer is treated with 5 N NaOH and extracted with diethyl ether. The organic layers are combined, concentrated, and chromatographed using silica gel, eluting with EtOAc in hexanes 0-40%, to give the title compound (1.27 g, 97% yield).

Aufarbeitung

  1. customAfter 1.25 hours the reaction is quenched with MeOH
  2. customThe two layers are separated
  3. additionthe aqueous layer is treated with 5 N NaOH
  4. extractionextracted with diethyl ether
  5. concentrationconcentrated
  6. customchromatographed
  7. washeluting with EtOAc in hexanes 0-40%

Quellen und Nachweise

ORD-Eintrag
ord-b3b7a539a342463ebf4536bb346429c8
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547691B2

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