(+/-)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropionamide → 3-(2-(Benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

HRID 1015580Notes

Reaction equation

HRID 1015580 reaction equation
[CH:1]([N:4]([CH:30]([CH3:32])[CH3:31])[C:5](=O)[CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:15]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1>O1CCCC1>[CH2:22]([O:21][C:15]1[CH:16]=[CH:17][C:18]([Br:20])=[CH:19][C:14]=1[CH:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH:30]([CH3:32])[CH3:31])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 22735207(+/-)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropionamideHCID 68718528lithium aluminium hydride THF

Product 1

HCID 129724153-(2-(Benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amineYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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).

Workup

  1. temperatureThe reaction was refluxed for 4 hrs
  2. customquenched with the dropwise addition of water
  3. customAfter removal of the precipitate the solvent
  4. customwas evaporated
  5. dissolutionthe oily residue dissolved in diluted sulphuric acid
  6. washThe aqueous phase was washed several times with diethyl ether
  7. extractionextracted with diethyl ether
  8. dry with materialThe extract was dried (sodium sulphate)
  9. filtrationfiltered
  10. customevaporated to dryness in vacuum

Sources & evidence

ORD record
ord-fe53c5c9f44e4ec89cf61c471032323c
Source dataset
uspto-grants-2011_07
Patent number
US07985772B2

Reaction notes

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