Triethylamine → HCID 89648928, compound

HRID 1773942Notes

Reaction equation

HRID 1773942 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][NH:10][CH2:9][CH2:8]2.C(N(CC)CC)C.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>C(Cl)Cl>[CH2:24]([O:23][C:21]([N:10]1[CH2:9][CH2:8][C:7]2[C:12](=[C:3]([OH:2])[CH:4]=[CH:5][CH:6]=2)[CH2:11]1)=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 136352151,2,3,4-Tetrahydroisoquinolin-8-ol--hydrogen chloride (1/1)

Product 1

HCID 89648928HCID 89648928, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an-ice cooled suspension of 8-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (746 mg, 5.0 mmol, 1.0 eq.) and triethylamine (2.13 mL, 15.0 mmol, 3.0 eq.) in DCM (25 mL), benzyl chloroformate (0.83 mL, 5.5 mmol, 1.1 eq.) was added dropwise. The solution was stirred at 0° C. for 1 hour and further at r.t. for 4 hours. The reaction was quenched with 1M aq. citric acid soln. (50 mL). The layers were separated. The aq. phase was extracted with DCM (3×50 mL). The comb. org. phases were dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in THF (20 mL) and 1M aq. NaOH soln. (6 mL) was added. The mixture was stirred at r.t. for 68 hours. The org. solvent was removed in vacuo. The resulting aq. layer was acidified with 2N aq. HCl soln. and extracted with DCM (3×25 ml). The comb. org. phases were dried over MgSO4 and concentrated in vacuo. The residue was purified by CC (SiO2, Hept/AcOEt 8:2 to 7:3) to give the title compound as a white solid.

Workup

  1. temperatureTo an-ice cooled
  2. additionwas added dropwise
  3. customThe reaction was quenched with 1M aq. citric acid soln
  4. customThe layers were separated
  5. extractionThe aq. phase was extracted with DCM (3×50 mL)
  6. dry with materialphases were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in THF (20 mL)
  9. addition(6 mL) was added
  10. stirringThe mixture was stirred at r.t. for 68 hours
  11. customsolvent was removed in vacuo
  12. extractionand extracted with DCM (3×25 ml)
  13. dry with materialphases were dried over MgSO4
  14. concentrationconcentrated in vacuo
  15. customThe residue was purified by CC (SiO2, Hept/AcOEt 8:2 to 7:3)

Sources & evidence

ORD record
ord-bfc907cb83da4ee481c1ce7bedfc3668
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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