反应 #979

反应方程式

3-indolebutyric acid

N,N-diisopropylethylamine

N,N-dimethylhydroxylamine hydrochloride

benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

→

amide

收率 94.3%

N-Methyl-N-Methoxy-4-(3-indolyl)butyramide

收率 94.3%

溶剂

acetonitrile

反应条件

后处理

1. 1
   浓缩was then concentrated to dryness
2. 2
   workup.DISSOLUTIONThe residue was dissolved into ethyl acetate
3. 3
   洗涤washed with water, 0.5N HCl, saturated NaHCO3 and brine
4. 4
   干燥dried over MgSO4
5. 5
   浓缩concentrated
6. 6
   洗涤Flash chromatography (elution with a gradient of 2-10% ether in methylene chloride)

实验过程

To a slurry of 1.75 g (8.61 mmol) of 3-indolebutyric acid (Aldrich Chemical Co.) in acetonitrile at room temperature was added 7.0 mL (40.2 mmol) of N,N-diisopropylethylamine, 1.0 g (10.3 mmol) of N,N-dimethylhydroxylamine hydrochloride and 4.19 g (9.5 mmol) of benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent) and the resulting mixture was allowed to stir at room temperature overnight and was then concentrated to dryness. The residue was dissolved into ethyl acetate and washed with water, 0.5N HCl, saturated NaHCO3 and brine and then dried over MgSO4 and concentrated. Flash chromatography (elution with a gradient of 2-10% ether in methylene chloride) provided 2.0 g of the amide 139. 1H NMR consistent with structure.

来源