反応 #78872

反応方程式

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

lithium aluminium hydride tetrahydrofuran

→

title compound

収率 76.7%

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

収率 76.7%

溶媒

tetrahydrofuran

反応条件

後処理

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

実験手順

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).

出典