Acetic Acid → (S)-(2-Chloro-3-trifluoromethyl-benzyl)(2-phenyl-propyl)-amine

HRID 902614Notes

Reaction equation

HRID 902614 reaction equation
[C:1]1([C@H:7]([CH3:10])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[Cl:15][C:16]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[Cl:15][C:16]1[C:23]([C:24]([F:25])([F:26])[F:27])=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH:9][CH2:8][C@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1547950(2S)-2-Phenylpropan-1-amineHCID 27366722-Chloro-3-(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68817028(S)-(2-Chloro-3-trifluoromethyl-benzyl)(2-phenyl-propyl)-amineYield 45.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-phenyl propylamine (0.5 g, 3.7 mmol) in dry dichloromethane was added acetic acid followed by 2-chloro-3-trifluoromethylbenzaldehyde (1.1 g, 5.5 mmol) and sodium triacetoxyborohydride (1.5 g, 7.4 mmol). After the resulting mixture was stirred for 1.5 h at RT water was added to quench the reaction. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The crude mixture was purified by column chromatograph (Ethyl acetate:Hexane/25:75) to give the title compound as an oil (0.55 g, 45%). MS (ESI) 327.6 (M+H)+.

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude mixture was purified by column chromatograph (Ethyl acetate:Hexane/25:75)

Sources & evidence

ORD record
ord-65e28c085ca94a75af6068ad954d4117
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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