Trifluoroacetic acid → HCID 18009179, compound

HRID 987569Notes

Reaction equation

HRID 987569 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH2:17][CH:16]2[N:18]([CH2:19][CH2:20][NH:21]C(=O)OC(C)(C)C)[CH:13]([CH2:14][CH2:15]2)[CH:12]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH2:12][CH:13]2[N:18]([CH2:19][CH2:20][NH2:21])[CH:16]([CH2:15][CH2:14]2)[CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18009168HCID 18009168, compound

Product 1

HCID 18009179HCID 18009179, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-[3-(2-naphthyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]ethylcarbamate (0.50 g, 1.30 mmol) and 1 mL trifluoroacetic acid are stirred at 23 C in 20 mL CH2Cl2 for 2 h. The volatiles are evaporated, and the residue is partitioned between 50 mL of saturated aqueous NaHCO3 and 50 mL EtOAc. The aqueous layer is extracted with 2×25 mL EtOAc, and the combined organics are washed with 3×50 mL H2O, 1×50 mL brine, dried over MgSO4, filtered, and evaporated to give 0.22g (0.79 mmol, a 60% yield) of the title compound as an orange solid. mp: 62-65 C; MS (ES) m/z 279 (MH)+.

Workup

  1. customThe volatiles are evaporated
  2. customthe residue is partitioned between 50 mL of saturated aqueous NaHCO3 and 50 mL EtOAc
  3. extractionThe aqueous layer is extracted with 2×25 mL EtOAc
  4. washthe combined organics are washed with 3×50 mL H2O, 1×50 mL brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give 0.22g (0.79 mmol

Sources & evidence

ORD record
ord-3fb767273cb04ccabe6d0c07f4129ec6
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Reaction notes

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