Reaktion #170149

Reaktionsgleichung

4-bromomethylpyridine hydrobromide

DIPEA

N-Boc-azetidin-3-ol

t-BuOK

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title product

Ausbeute 41.0%

tert-Butyl 3-(pyridin-4-ylmethoxy)azetidine-1-carboxylate

Ausbeute 41.0%

Lösungsmittel

H2O

dichloromethane

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Temperaturthen cooled to 0° C
3. 3
   workup.ADDITIONwas then added
4. 4
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 24 h
5. 5
   Extraktionextracted twice with EtOAc
6. 6
   SonstigeThe organics were separated from the aqueous layer
7. 7
   Trocknendried over Na2SO4
8. 8
   Einengenconcentrated to dryness
9. 9
   SonstigeThe crude mixture was purified by column chromatography (eluent: Pentane/EtOAc, 1/1 to 7/3)

Vorschrift

A solution of N-Boc-azetidin-3-ol (500 mg, 2.89 mmol) in THF (10 mL) was cooled to 0° C. t-BuOK (1M in THF, 11.6 mL) was added dropwise and the reaction mixture was stirred at room temperature for 0.25 h then cooled to 0° C. A solution of 4-bromomethylpyridine hydrobromide (2.19 g, 8.67 mmol) in dichloromethane (5 mL) stirred with DIPEA (4 mL, 24 mmol) for 0.5 h was then added. The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with H2O and extracted twice with EtOAc. The organics were separated from the aqueous layer and combined, dried over Na2SO4 and concentrated to dryness. The crude mixture was purified by column chromatography (eluent: Pentane/EtOAc, 1/1 to 7/3) to give the title product (313 mg, 41%) as a yellow oil.

Quelle