Réaction #78872

Équation de réaction

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

lithium aluminium hydride tetrahydrofuran

→

title compound

Rendement 76.7%

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

Rendement 76.7%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was refluxed for 4 hrs
2. 2
   Autrequenched with the dropwise addition of water
3. 3
   AutreAfter removal of the precipitate the solvent
4. 4
   Autrewas evaporated
5. 5
   workup.DISSOLUTIONthe oily residue dissolved in diluted sulphuric acid
6. 6
   LavageThe aqueous phase was washed several times with diethyl ether
7. 7
   Extractionextracted with diethyl ether
8. 8
   SéchageThe extract was dried (sodium sulphate)
9. 9
   Filtrationfiltered
10. 10
    Autreevaporated to dryness in vacuum

Mode opératoire

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).

Source