Trifluoromethanesulfonic acid → HCID 66942366, compound

HRID 536673Notes

Reaction equation

HRID 536673 reaction equation
FC(F)(F)S(O)(=O)=O.C(OC([N:16]1[CH:22]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[C:20]([CH3:30])[CH2:19][CH2:18][CH2:17]1)=O)(C)(C)C>ClCCl>[CH3:30][C:20]12[CH2:21][CH:22]([NH:16][CH2:17][CH2:18][CH2:19]1)[CH2:23][C:24]1[C:25]2=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 58123760HCID 58123760, compound

Product 1

HCID 66942366HCID 66942366, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic acid (2.5 mL) is added to a solution of 7-benzyl-5-methyl-2,3,4,7-tetrahydro-azepine-1-carboxylic acid tert-butyl ester (0.30 g) in dichloromethane (5 mL) chilled in an ice bath. The ice bath is removed and the solution is stirred at room temperature for 5 h. Then, ice-cold water and aqueous K2CO3 solution are added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4), the solvent is evaporated, and the residue is purified by chromatography on silica gel (dichloroemethane/methanol 99:1->9:1).

Workup

  1. temperaturechilled in an ice bath
  2. customThe ice bath is removed
  3. additionThen, ice-cold water and aqueous K2CO3 solution are added
  4. extractionthe resulting mixture is extracted with ethyl acetate
  5. dry with materialThe combined extracts are dried (Na2SO4)
  6. customthe solvent is evaporated
  7. customthe residue is purified by chromatography on silica gel (dichloroemethane/methanol 99:1->9:1)

Sources & evidence

ORD record
ord-39b8c93c7a1340daba25df24a269e58e
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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