Trifluoroacetic acid → 1-(2-Amino-4-chloro-5-methoxyphenyl)-3-methylpentan-2-ol

HRID 2400286Notes

Reaction equation

HRID 2400286 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][CH3:16])=[CH:10][C:9]=1[CH2:17][CH:18]([OH:23])[CH:19]([CH3:22])[CH2:20][CH3:21])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][CH3:16])=[CH:10][C:9]=1[CH2:17][CH:18]([OH:23])[CH:19]([CH3:22])[CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131731723HCID 131731723, compound

Product 1

HCID 696710981-(2-Amino-4-chloro-5-methoxyphenyl)-3-methylpentan-2-olYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[5-chloro-2-(2-hydroxy-3-methylpentyl)-4-methoxyphenyl]carbamate (873 mg) in dichloromethane (12.2 mL) was added dropwise trifluoroacetic acid (3.76 mL) under ice-cooling, and this mixture was stirred for 9 hours. The reaction mixture was concentrated under reduced pressure. To the residue were added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution to separate the organic layer. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (603 mg). 1H-NMR (CDCl3) δ ppm: 0.75-1.75 (9H, m), 2.45-2.85 (2H, m), 3.30-4.10 (6H, m), 6.60-6.80 (2H, m). ESI-MS (m/z): 258, 260 (M+H)+

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue were added ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  4. customto separate the organic layer
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-355b552f146d4cc6a81560c75557cbfa
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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