Реакция #218952

Уравнение реакции

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

lithium aluminium hydride tetrahydrofuran

→

title compound

Выход 76.7%

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

Выход 76.7%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was refluxed for 4 hrs
2. 2
   Другоеquenched with the dropwise addition of water
3. 3
   ДругоеAfter removal of the precipitate the solvent
4. 4
   Другоеwas evaporated
5. 5
   workup.DISSOLUTIONthe oily residue dissolved in diluted sulphuric acid
6. 6
   ПромывкаThe aqueous phase was washed several times with diethyl ether
7. 7
   Экстракцияextracted with diethyl ether
8. 8
   СушкаThe extract was dried (sodium sulphate)
9. 9
   Фильтрацияfiltered
10. 10
    Другоеevaporated to dryness in vacuum

Методика

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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