Trifluoroacetic acid → HCID 12943342, compound

HRID 659132

Reaction equation

HRID 659132 reaction equation
[C:1]1([CH:7]([NH:11]C(=O)OC(C)(C)C)[CH2:8][C:9]#[CH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[C:1]1([CH:7]([NH2:11])[CH2:8][C:9]#[CH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57429813Tert-butyl (1-phenylbut-3-yn-1-yl)carbamate2×

Product 1

HCID 12943342HCID 12943342, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.03 g of tert-butyl 1-phenylbut-3-ynylcarbamate (Formula 16) in 15 mL of dichloromethane was added 3 mL of trifluoroacetic acid. The mixture was stirred at room temperature for 1 hour. Then, dichloromethane was removed. The residue was diluted with water and extracted with ethyl acetate. Combined ethyl acetate was washed with brine, dried over sodium sulfate and concentrated. Column chromatography (60% ethyl acetate/hexane) gave 564 mg (93%) of 1-phenylbut-3-yn-1-amine (Formula 17) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 2.04-2.05 (m, 1H), 2.43-2.63 (m, 2H), 4.14-4.19 (m, 1H), 7.24-7.40 (m, 5H).

Workup

  1. customThen, dichloromethane was removed
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washCombined ethyl acetate was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0e2bc74570eb498687da572516211016
Source dataset
uspto-grants-2011_12
Patent number
US08080570B2

Linked notes

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