Benzyl chloroformate → HCID 59205695, compound

HRID 1807475Notes

Reaction equation

HRID 1807475 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[H-].[Na+].[CH2:14]([O:21][C:22](Cl)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH2:14]([O:21][C:22](=[O:23])[NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 5889916-Aminoisoquinoline

Product 1

HCID 59205695HCID 59205695, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 6-aminoisoquinoline in DMF at −40° C. was added NaH and solution was warmed to 0° C. for 30 minutes. Then benzylchloroformate was added and the reaction stirred at 0° C. for 2 hours. The solution was quenched with AcOH, poured into NaHCO3(sat) and extracted with EtOAc, dried (Na2SO4), filtered and evaporated. Flash chromatography (SiO2 90% EtOAc/Hex) gave benzylisoquinolin-6-ylcarbamate. (E87).

Workup

  1. customThe solution was quenched with AcOH
  2. additionpoured into NaHCO3(sat)
  3. extractionextracted with EtOAc
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-78b3c9563f17475aa30c769eb444a591
Source dataset
uspto-grants-2013_01
Patent number
US08357699B2

Reaction notes

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