Water → (alphaS)-alpha-[Bis(phenylmethyl)amino]benzenepropanal

HRID 732346Notes

Reaction equation

HRID 732346 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.O>CS(C)=O.C(OCC)(=O)C>[CH2:19]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH:10]=[O:11])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 7019180(S)-(+)-2-(Dibenzylamino)-3-phenyl-1-propanol

Product 1

HCID 9883943(alphaS)-alpha-[Bis(phenylmethyl)amino]benzenepropanal

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2-(S)-dibenzylamino-3-phenylpropan-1-ol (5.00 g, 15.08 mmol) in dimethylsulfoxide (DMSO) (15 mL) and cool in an ice bath. Add triethylamine (8.4 mL, 60.0 mmol) followed by sulfur trioxide-pyridine complex (4.80 g, 30.2 mmol). Stir 30 min then slowly add water (15 mL). Dilute with ethyl acetate and wash with 5% aqueous citric acid (3×), saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound as a light yellow residue.

Workup

  1. temperaturecool in an ice bath
  2. washwash with 5% aqueous citric acid (3×), saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-7aca519e04da48a8bc6ed264b0dbc18a
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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