Trifluoroacetic acid → 3-(5,6,7,8,9,10-Hexahydro[1,2,4]triazolo[4,3-a]azocin-3-yl)-3-(2-thienyl)cyclobutanol

HRID 502984Notes

Reaction equation

HRID 502984 reaction equation
COC[O:4][CH:5]1[CH2:8][C:7]([C:14]2[N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:17]3=[N:16][N:15]=2)([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH2:6]1.FC(F)(F)C(O)=O>C(Cl)Cl>[N:16]1[N:15]=[C:14]([C:7]2([C:9]3[S:10][CH:11]=[CH:12][CH:13]=3)[CH2:6][CH:5]([OH:4])[CH2:8]2)[N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:17]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 684676073-[3-(Methoxymethoxy)-1-(2-thienyl)cyclobutyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine

Product 1

HCID 590064423-(5,6,7,8,9,10-Hexahydro[1,2,4]triazolo[4,3-a]azocin-3-yl)-3-(2-thienyl)cyclobutanolYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[3-(Methoxymethoxy)-1-(2-thienyl)cyclobutyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (6.14 g) was dissolved in methylene chloride (125 ml) and then trifluoroacetic acid (25 ml) was added thereto, followed by stirring at room temperature for 21 hours. The reaction solution was subjected to evaporation under reduced pressure and the resulting residue was diluted with a 1M aqueous sodium hydroxide solution (100 ml), followed by extraction with chloroform (100 ml×2). The organic layer was dried over anhydrous sodium sulfate, and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting solid washed with diethyl ether to obtain 3.84 g of 3-(5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocin-3-yl)-3-(2-thienyl)cyclobutanol (white solid).

Workup

  1. customThe reaction solution was subjected to evaporation under reduced pressure
  2. additionthe resulting residue was diluted with a 1M aqueous sodium hydroxide solution (100 ml)
  3. extractionfollowed by extraction with chloroform (100 ml×2)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed by evaporation under reduced pressure
  7. washThe resulting solid washed with diethyl ether

Sources & evidence

ORD record
ord-0d29b3e4f63c4b3881bcca1f1d69f4d3
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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