Reaktion #10022

Reaktionsgleichung

(S)-2-(tert-butoxycarbonyl)aminobutyraldehyde

oxazolo[4,5-b]pyridine

Isopropylmagnesium chloride

→

desired compound

Ausbeute 43.5%

(S)-2-(tert-butoxycarbonyl)amino-1-(oxazolo[4,5-b]pyridin-2-yl)propan-1-ol

Ausbeute 43.5%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a clean roundbottom flask equipped
2. 2
   workup.STIRRINGAfter stirring for 1 h at 0° C.
3. 3
   SonstigeThe ice bath was removed
4. 4
   Temperaturto warm to room temperature
5. 5
   Sonstigethe reaction mixture was quenched with saturated ammonium chloride solution
6. 6
   Einengenconcentrated to dryness
7. 7
   ExtraktionThe residue was extracted with EtOAc
8. 8
   Waschenwashed with brine
9. 9
   Sonstigedried with anhyd
10. 10
    FiltrationMgSO4, filtered
11. 11
    Einengenconcentrated
12. 12
    SonstigeThe crude product was purified by chromatograph

Vorschrift

In a clean roundbottom flask equipped with stir bar was placed oxazolo[4,5-b]pyridine (600 mg, 5 mmol) in 30 mL THF and the reaction mixture was cooled to 0° C. under N2 atmosphere. Isopropylmagnesium chloride (2M in THF, 2.5 ml, 5 mmol ) was added. After stirring for 1 h at 0° C., (S)-2-(tert-butoxycarbonyl)aminobutyraldehyde (573 mg, 3 mmol) in 20 ml THF was added. The ice bath was removed and the reaction mixture was allowed to warm to room temperature. After 2 h, the reaction mixture was quenched with saturated ammonium chloride solution and concentrated to dryness. The residue was extracted with EtOAc, then washed with brine, dried with anhyd. MgSO4, filtered and concentrated. The crude product was purified by chromatograph to yield 383 mg of the desired compound.

Quelle