Reaktion #74484

Reaktionsgleichung

(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)(6-ethoxypyridazin-3-yl)methanone

NaBH4

→

title compound

(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)(6-ethoxypyridazin-3-yl)methanol

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with 2N HCl
2. 2
   Extraktionextracted with ethyl acetate (3×50 mL)
3. 3
   Waschenwashed with brine
4. 4
   TrocknenThe organic layer was dried over MgSO4
5. 5
   Sonstigethe solvents were evaporated under a vacuum
6. 6
   SonstigeThe crude mixture was further purified by flash column chromatography (Biotage SP1™) (eluent: hexane/EtOAc mixture (40/60; v/v))

Vorschrift

To a solution of (2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)(6-ethoxypyridazin-3-yl)methanone (970 mg; 1.24 mmol) in MeOH (20 mL) was added NaBH4 (93.5 mg; 2.47 mmol) at 0° C., then stirred for 3 h at room temperature. The reaction was quenched with 2N HCl, extracted with ethyl acetate (3×50 mL) and washed with brine. The organic layer was dried over MgSO4 and the solvents were evaporated under a vacuum. The crude mixture was further purified by flash column chromatography (Biotage SP1™) (eluent: hexane/EtOAc mixture (40/60; v/v)) to obtain 907 mg (1.15 mmol; 93%) of the title compound as colorless oil.

Quelle