2-Azidomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine → 2-Aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine

HRID 473223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 473223
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[N:6]=1)=[N+]=[N-]>CO.[Pd].NCCN>[NH2:1][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])[N:6]=1

Komponenten

4

Edukt 1

HCID 866715132-Azidomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine

Produkt 1

HCID 668467232-Aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridineAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11513808Pd/C(en)KatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A suspension of 2-azidomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine (2) (0.83 g, 2.98 mmol) and 5% Pd/C(en) (83.0 mg, 10 wt %) in MeOH (20 mL) was vigorously stirred for 5 hours at a room temperature under a hydrogen atmosphere. TLC was used to confirm there was no starting material in the reaction mixture. Then, the catalyst was removed by suction filtration with a kiriyama funnel. The filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3:MeOH=30:1 to 10:1) to give 2-aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine (3) (603 mg, 80%) as a yellow oil.

Aufarbeitung

  1. customThen, the catalyst was removed by suction filtration with a kiriyama funnel
  2. customThe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (CHCl3:MeOH=30:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-706b3643cbae439a9dde7df6ab9d9b98
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633304B2

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