Trifluoroacetic acid → 3'-Benzyloxybiphenyl-4-ylmethylamine

HRID 1713272Notes

Reaction equation

HRID 1713272 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][NH:22]C(=O)OC(C)(C)C)=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][NH2:22])=[CH:19][CH:20]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67454416HCID 67454416, compound

Product 1

HCID 230050193'-Benzyloxybiphenyl-4-ylmethylamineYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of tert-butyl N-(3′-benzyloxy-biphenyl-4-ylmethyl)carbamate (0.500 g) in dichloromethane (2.6 mL) was added trifluoroacetic acid (0.976 mL), and the resulting mixture was stirred under ice-cooling for 1 hour. Saturated aqueous sodium hydrogen carbonate (15 mL) was added dropwise and the whole was extracted with dichloromethane (30 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate/brine (1/1, 10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (0.367 g).

Workup

  1. temperaturecooling for 1 hour
  2. extractionthe whole was extracted with dichloromethane (30 mL)
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate/brine (1/1, 10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ea69066c9af4d008abfc0dd06b1fa41
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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