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

HRID 902669Notes

Reaction equation

HRID 902669 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.[Cl:11][C:12]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCl.C(O)(=O)C.CCCCCC>[Cl:11][C:12]1[C:19]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][NH:9][CH2:8][C@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:10]

Participants

8

Reactant 4

HCID 962WaterHCID 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 3

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of (S)-(−)-2-phenyl propylamine (0.5 g, 3.7 mmol) in dry dichloromethane (100 ml) was added acetic acid (2 drops) 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 room temperature, water was added to quench the reaction. The aqueous layer was extracted with ethyl acetate. The combined organic layers was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude mixture was purified by silica gel column chromatograph using EtOAc:Hexane/25:75 as the eluant to give 0.55 g (45% yield) of the title compound as an oil. MS m/e327.6 (M+H)+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude mixture was purified by silica gel column chromatograph

Sources & evidence

ORD record
ord-93d9750018f141909b34e17153782600
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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