تفاعل #822893

معادلة التفاعل

NaHCO3

glycine benzyl ester hydrochloride

4-bromobenzaldehyde

acetic acid

Sodium triacetoxyborohydride

→

80A

المردود 64.0%

benzyl 2-(4-bromobenzylamino)acetate

المردود 64.0%

المذيبات

DCE

ظروف التفاعل

المعالجة

1. 1
   أخرىto give a clear solution
2. 2
   استخلاصextracted with CH2Cl2 (3×)
3. 3
   استخلاصThe combined organic extract
4. 4
   غسيلwashed with brine
5. 5
   تجفيفdried (Na2SO4)
6. 6
   تركيزconcentrated
7. 7
   أخرىThe crude product was purified via flash chromatography (0 to 100% EtOAc in hexanes)

الإجراء التجريبي

To a suspension of glycine benzyl ester hydrochloride (2.02 g, 10.0 mmol) and 4-bromobenzaldehyde (1.85 g, 10.0 mmol) in 50 mL DCE, was added acetic acid (2.9 mL, 50 mmol) and TEA (1.4 mL, 10.0 mmol) to give a clear solution. Sodium triacetoxyborohydride (4.24 g, 20.0 mmol) was added. The suspension was stirred at rt for 17 h. The mixture was neutralized with sat. NaHCO3 and extracted with CH2Cl2 (3×). The combined organic extract washed with brine, dried (Na2SO4) and concentrated. The crude product was purified via flash chromatography (0 to 100% EtOAc in hexanes) to afford 80A (2.13 g, 64%). MS (ESI) m/z 334.0 (M+H)+.

المصدر