N-[2-(4-benzyloxylphenyl)-2-hydroxyethyl)propionamide → 1-(4-Benzyloxyphenyl)-2-propylaminoethanol

HRID 2252633Notes

Reaction equation

HRID 2252633 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:22])[CH2:16][NH:17][C:18](=O)[CH2:19][CH3:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([OH:22])[CH2:16][NH:17][CH2:18][CH2:19][CH3:20])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 59645258N-[2-(4-benzyloxylphenyl)-2-hydroxyethyl)propionamide

Product 1

HCID 574406901-(4-Benzyloxyphenyl)-2-propylaminoethanolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the amide from example 25 (27.5 g, 0.092 mol) in dry THF (100 ml) was added borane-methyl sulphide complex (17.5 ml, 0.18 mol) and the reaction mixture was stirred at reflux for 2 hours. The reaction mixture was cooled then quenched with methanol (30 ml). Water (50 ml) and c.HCl (35 ml) were added and the reaction mixture stirred until all bubbling ceased before concentrating in vacuo. To the residue water (250 ml) was added, before basifying by addition of NH4OH (30 ml). The aqueous layer was extracted with ethyl acetate (3×200 ml) and the combined organic extracts dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the title compound as a white solid (26.1 g, 0.09 mol, 99%). 1H NMR (CD3OD, 400 MHz) δ: 0.95 (t, 3H), 1.58 (q, 2H), 2.62 (m, 2H), 2.81 (m, 2H), 4.72 (dd, 1H), 5.05 (s, 2H), 6.95 (d, 2H), 7.24 (m, 3H), 7.35 (t, 2H), 7.41 (d, 2H). LRMS: m/z 286 (M−H+).

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. customthen quenched with methanol (30 ml)
  4. additionHCl (35 ml) were added
  5. stirringthe reaction mixture stirred until all bubbling
  6. concentrationbefore concentrating in vacuo
  7. additionTo the residue water (250 ml) was added
  8. additionbefore basifying by addition of NH4OH (30 ml)
  9. extractionThe aqueous layer was extracted with ethyl acetate (3×200 ml)
  10. dry with materialthe combined organic extracts dried over anhydrous magnesium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b72d3bba9894f23863a976d347632bc
Source dataset
uspto-grants-2008_01
Patent number
US07323462B2

Reaction notes

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