Reaction #78872

Reaction equation

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

lithium aluminium hydride tetrahydrofuran

→

title compound

Yield 76.7%

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

Yield 76.7%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureThe reaction was refluxed for 4 hrs
2. 2
   Otherquenched with the dropwise addition of water
3. 3
   OtherAfter removal of the precipitate the solvent
4. 4
   Otherwas evaporated
5. 5
   workup.DISSOLUTIONthe oily residue dissolved in diluted sulphuric acid
6. 6
   WashThe aqueous phase was washed several times with diethyl ether
7. 7
   Extractionextracted with diethyl ether
8. 8
   DryingThe extract was dried (sodium sulphate)
9. 9
   Filtrationfiltered
10. 10
    Otherevaporated to dryness in vacuum

Procedure

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