Benzylamine → (1S)-1-(4-fluorophenyl)-2-(benzylamino)ethanol

HRID 1671472Notes

Reaction equation

HRID 1671472 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][O:9]2)=[CH:4][CH:3]=1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([OH:9])[CH2:10][NH:18][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 11228840(S)-(4-Fluorophenyl)oxirane

Product 1

HCID 15983828(1S)-1-(4-fluorophenyl)-2-(benzylamino)ethanolYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (2S)-2-(4-fluorophenyl)oxirane (8.28 g) and benzylamine (19.3 g, 180 mmol) was heated at 80° C. for 4 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate. After removal of the solvent, the precipitate was collected by filtration and washed with hexane to give (1S)-1-(4-fluorophenyl)-2-(benzylamino)ethanol (8.3 g) as white crystals (yield 57% for 3 steps).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removal of the solvent
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with hexane

Sources & evidence

ORD record
ord-09500e101e5f441aa3c276890e565134
Source dataset
uspto-grants-2011_08
Patent number
US07994315B2

Reaction notes

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