Triethylamine → 2-tert-butyl 6-methyl 3,4-dihydroisoquinoline-2,6(1H)-dicarboxylate

HRID 352858Notes

Reaction equation

HRID 352858 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:6]([O:5][CH3:1])=[O:7])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 10091216Tert-butyl 6-(trifluoromethylsulfonyloxy)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 114831762-tert-butyl 6-methyl 3,4-dihydroisoquinoline-2,6(1H)-dicarboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

In methanol (50 ml), 2-tert-butoxycarbonyl-6-trifluoromethanesulfonyloxy-1,2,3,4-tetrahydroisoquinoline (1.34 g) was dissolved, followed by the addition of triethylamine (0.73 ml), palladium (II) acetate (40 mg) and 1,3-(diphenylphosphino)propane (145 mg). Under a carbon monoxide gas stream, the resulting mixture was stirred overnight at 70° C. The reaction mixture was concentrated under reduce pressure and the residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=15:1), whereby the title compound (665 mg, 65%) was obtained.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=15:1), whereby the title compound (665 mg, 65%)
  3. customwas obtained

Sources & evidence

ORD record
ord-86ed57b63d424d6cae3a36825d3afd5a
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…