(E)-3-(tert-Butoxycarbonylamino-methyl)-6-(2-cyclohexylvinyl)-pyridine → HCID 58495451, compound

HRID 1190988Notes

Reaction equation

HRID 1190988 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:11]=[N:12][C:13](/[CH:16]=[CH:17]/[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:15]=1)=O)(C)(C)C>CCOC(C)=O>[NH2:8][CH2:9][C:10]1[CH:11]=[N:12][C:13](/[CH:16]=[CH:17]/[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 58495588(E)-3-(tert-Butoxycarbonylamino-methyl)-6-(2-cyclohexylvinyl)-pyridine

Product 1

HCID 58495451HCID 58495451, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dissolve (E)-3-(tert-butoxycarbonylamino-methyl)-6-(2-cyclohexylvinyl)-pyridine (1.3 g, 4.11 mmol) in EtOAc (60 mL) and bubble hydrogen chloride through the solution for 20 min. Stir the mixture overnight at room temperature. Concentrate the mixture in vacuo and dissolve the resulting solid in water. Adjust the pH to 9-11 with 20% aqueous K2CO3 and extract with DCM. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo to obtain the title compound (0.78 g, 88%). MS (APCI+) m/z: 217 (M+H)+.

Workup

  1. custombubble hydrogen chloride through the solution for 20 min
  2. concentrationConcentrate the mixture in vacuo
  3. dissolutiondissolve the resulting solid in water
  4. extractionextract with DCM
  5. dry with materialDry the combined organic extracts over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-5555a9ffd37f44fbb2edf2f6b4e2a739
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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