Triethylamine → HCID 178511556, compound

HRID 1524863Notes

Reaction equation

HRID 1524863 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9]C(=O)OC(C)(C)C)[CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>C(Cl)Cl>[NH2:9][C@H:6]1[CH2:5][CH2:4][C@H:3]([CH2:2][NH:1][C:25](=[O:26])[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 178453944HCID 178453944, compound

Product 1

HCID 178511556HCID 178511556, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

t-Butyl trans-4-aminomethylcyclohexylcarbamate (344 mg, 1.5 mmol) was dissolved in CH2Cl2 (7 mL) and cooled in an ice-bath. Triethylamine (0.21 mL, 1.5 mmol) was added, followed by benzyl chloroformate (0.22 mL, 1.5 mmol) dropwise. The mixture was stirred at rt under N2 for 2 h. The reaction mixture was diluted with CH2Cl2 and washed with water and brine, dried over Na2SO4, filtered, and concentrated to a white solid. This solid was dissolved in 10 mL of 4 N HCl-dioxane and stirred at rt for 10 min. The solvent was removed. The residue was dried under vacuum to give 350 mg of the desired product as a white solid (78%). MS 263.36 (M+H)+.

Workup

  1. temperaturecooled in an ice-bath
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to a white solid
  6. dissolutionThis solid was dissolved in 10 mL of 4 N HCl-dioxane
  7. stirringstirred at rt for 10 min
  8. customThe solvent was removed
  9. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-7a64aab8eb8047928f1f4f787c05706a
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

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