反应 #78872

反应方程式

(±)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropionamide

lithium aluminium hydride tetrahydrofuran

→

title compound

收率 76.7%

(±)-[3-(2-Benzyloxy-5-bromophenyl)-3-phenylpropyl]-diisopropylamine

收率 76.7%

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   温度The reaction was refluxed for 4 hrs
2. 2
   其他quenched with the dropwise addition of water
3. 3
   其他After removal of the precipitate the solvent
4. 4
   其他was evaporated
5. 5
   workup.DISSOLUTIONthe oily residue dissolved in diluted sulphuric acid
6. 6
   洗涤The aqueous phase was washed several times with diethyl ether
7. 7
   萃取extracted with diethyl ether
8. 8
   干燥The extract was dried (sodium sulphate)
9. 9
   过滤filtered
10. 10
    其他evaporated to dryness in vacuum

实验过程

To a stirred solution of (±)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropionamide (11.8 g) in 40 ml of dry tetrahydrofuran was added 1 M lithium aluminium hydride/tetrahydrofuran (36 ml). The reaction was refluxed for 4 hrs and then quenched with the dropwise addition of water. After removal of the precipitate the solvent was evaporated and the oily residue dissolved in diluted sulphuric acid. The aqueous phase was washed several times with diethyl ether, adjusted to pH 10-12 (aqueous NaOH), and extracted with diethyl ether. The extract was dried (sodium sulphate), filtered and evaporated to dryness in vacuum to leave 8.1 g (76.7%) of the title compound as a viscous colourless oil, tlc: (4) 0.86. The NMR spectrum corresponds to the product, obtained from the tosylate precursor (see above).

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