2-(3-Fluorophenyl)ethanamine → HCID 58276383, compound

HRID 471869Notes

Reaction equation

HRID 471869 reaction equation
[CH:1]([C:3]1[O:7][C:6]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)=O.[F:19][C:20]1[CH:21]=[C:22]([CH2:26][CH2:27][NH2:28])[CH:23]=[CH:24][CH:25]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[F:19][C:20]1[CH:21]=[C:22]([CH2:26][CH2:27][NH:28][CH2:1][C:3]2[O:7][C:6]([C:8]3[CH:9]=[CH:10][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17][CH:18]=3)=[CH:5][CH:4]=2)[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 5339282-(3-Fluorophenyl)ethanamineHCID 608139Benzoic acid, 4-(5-formyl-2-furanyl)-, ethyl esterHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58276383HCID 58276383, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a 100 mL round bottom flask was added ethyl 4-(5-formyl-2-furanyl)benzoate (100 mg, 0.41 mmol, commercially available), [2-(3-fluorophenyl)ethyl]amine (0.070 mL, 0.49 mmol), NaBH(OAc)3 (261 mg, 1.23 mmol) and DCE (10 mL). The reaction was stirred at room temperature overnight, quenched with H2O, and extracted with CH2Cl2 (×3). The organic layer was washed with brine, dried with MgSO4 and concentrated under reduced pressure to give 150 mg of ethyl 4-[5-({[2-(3-fluorophenyl)-ethyl]amino}methyl)-2-furanyl]benzoate (used without further purification). LC/MS (method A) 1.97 min; m/z 368 (M+H).

Workup

  1. customquenched with H2O
  2. extractionextracted with CH2Cl2 (×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0adf4dabf41d43169400979128936508
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Reaction notes

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