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

HRID 880228Notes

Reaction equation

HRID 880228 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>>[CH2:11]([NH:18][CH2:10][C@H:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[OH:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

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

Product 1

HCID 15983828(1S)-1-(4-fluorophenyl)-2-(benzylamino)ethanolYield 77.7%

Conditions

Temperature
80 °C

Procedure

Charge a 10 L round bottom flask with (S)-2-(4-fluorophenyl)oxirane (880 g, 6.38 mol) under a nitrogen atmosphere. Add benzylamine (2047 g, 19.13 mol) while the mixture is maintained at 20° C. Heat the mixture to 80° C. and stir it at that temperature for 5 h. Cool to 22° C. and stir for 16 h. Add H2O (3 L) to quench the reaction. Filter and wash the filter cake with water (2×1 L). Slurry the solid obtained with heptane (2 L) and filter to give the title compound (1216 g, 77%). MS (m/z): 246 (M+1); ee value: 99.0% (AD-H 250 mm×4.6 mm×5 μm column using 90:10 hexanes (with 0.02% diethylamine):EtOH at 25° C. with a flow rate of 1.0 mL/min).

Workup

  1. temperatureCool to 22° C.
  2. stirringstir for 16 h
  3. customAdd H2O (3 L) to quench
  4. customthe reaction
  5. filtrationFilter
  6. washwash the filter cake with water (2×1 L)
  7. customobtained with heptane (2 L)
  8. filtrationfilter

Sources & evidence

ORD record
ord-266ec4d4051146268aac4ccd8b16c8c4
Source dataset
uspto-grants-2015_03
Patent number
US08993568B2

Reaction notes

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