Dibenzylamine → (2S)-1-(dibenzylamino)-3-phenoxy-2-propanol

HRID 47671Notes

Reaction equation

HRID 47671 reaction equation
[O:1]([CH2:8][C@@H:9]1[CH2:11][O:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[CH2:20]([N:19]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:11][C@H:9]([OH:10])[CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 1534345(2S)-2-(phenoxymethyl)oxirane

Product 1

HCID 10154726(2S)-1-(dibenzylamino)-3-phenoxy-2-propanolYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction mixture containing (2S)-2-(phenoxymethyl)oxirane (Example 15, 20.6 mmol, 1.0 eq.) and dibenzylamine (22.7 mmol, 1.1 eq.) in MeOH (100 mL) was heated at reflux overnight. The resulting solution was concentrated in vacuo and the crude product was purified by medium pressure column chromatography (Biotage 40S normal phase silica gel column, hexanes:EtOAc=10:1). The product was obtained as a colorless oil in 88% yield. MH+=348.3, Rf=0.42 (hexanes:EtOAc 6:1), retention time (LC-MS)=2.22 min.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe resulting solution was concentrated in vacuo
  4. customthe crude product was purified by medium pressure column chromatography (Biotage 40S normal phase silica gel column, hexanes:EtOAc=10:1)
  5. customThe product was obtained as a colorless oil in 88% yield

Sources & evidence

ORD record
ord-ff620d44e85e4f14a9188448bcb4dd73
Source dataset
uspto-grants-2004_03
Patent number
US06699860B2

Reaction notes

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