反应 #1007150

反应方程式

(R)-4-[1-(1-phenyl-ethylamino)-ethylidene]-pent-2-enedioic acid dimethyl ester

NaOMe

N-bromosuccinimide

→

title compound

收率 51.8%

(R)-5-Bromo-2-methyl-6-oxo-1-(1-phenyl-ethyl)-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

收率 51.8%

溶剂

MeOH

反应条件

后处理

1. 1
   温度the resulting mixture was refluxed for 7 h
2. 2
   其他the solvent was evaporated in vacuo
3. 3
   workup.ADDITIONSaturated NH4Cl was added
4. 4
   萃取the resulting mixture was extracted with CH2Cl2
5. 5
   干燥The organic layer was dried over MgSO4
6. 6
   浓缩concentrated
7. 7
   其他The crude product was chromatographed (0-25% EtOAc/hexanes)

实验过程

MeOH (170 mL) was added to a flask containing (R)-4-[1-(1-phenyl-ethylamino)-ethylidene]-pent-2-enedioic acid dimethyl ester (5.56 g, 18.3 mmol). NaOMe solution (4.2 mL, 18.3 mmol, 4.375 M in MeOH) and N-bromosuccinimide (3.92 g, 22 mmol) were added, and the resulting mixture was refluxed for 7 h. After cooling to r.t., the solvent was evaporated in vacuo. Saturated NH4Cl was added, and the resulting mixture was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The crude product was chromatographed (0-25% EtOAc/hexanes) to give 3.32 g of the title compound as an off-white solid. MS: (+) m/z 372.20, 374.16 (M+Na, 79/81Br).

来源