تفاعل #10022

معادلة التفاعل

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

oxazolo[4,5-b]pyridine

Isopropylmagnesium chloride

→

desired compound

المردود 43.5%

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

المردود 43.5%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىIn a clean roundbottom flask equipped
2. 2
   workup.STIRRINGAfter stirring for 1 h at 0° C.
3. 3
   أخرىThe ice bath was removed
4. 4
   درجة الحرارةto warm to room temperature
5. 5
   أخرىthe reaction mixture was quenched with saturated ammonium chloride solution
6. 6
   تركيزconcentrated to dryness
7. 7
   استخلاصThe residue was extracted with EtOAc
8. 8
   غسيلwashed with brine
9. 9
   أخرىdried with anhyd
10. 10
    ترشيحMgSO4, filtered
11. 11
    تركيزconcentrated
12. 12
    أخرىThe crude product was purified by chromatograph

الإجراء التجريبي

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.

المصدر