Trifluoroacetic acid → Methyl 1,2,3,4-tetrahydroisoquinoline-7-carboxylate

HRID 2036883Notes

Reaction equation

HRID 2036883 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH2:4][CH2:3][N:2]1C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH2:4][CH2:3][NH:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 594838422-Tert-butyl 7-methyl 3,4-dihydroisoquinoline-2,7(1H)-dicarboxylate

Product 1

HCID 10656920Methyl 1,2,3,4-tetrahydroisoquinoline-7-carboxylateYield 199.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C. a mixture of 16.93 g 2-tert-butyl 7-methyl 3,4-dihydroisoquinoline-2,7(1H)-dicarboxylate, 160 ml dichloromethane and 80 ml trifluoroacetic acid is stirred for 30 min. Then, the mixture is stirred for 5 h at ambient temperature. The reaction mixture is evaporated and the residue is treated with a 10% KOH solution and dichloromethane. The organic layer is dried and evaporated. 22.18 g of the title compound are obtained.

Workup

  1. stirringThen, the mixture is stirred for 5 h at ambient temperature
  2. customThe reaction mixture is evaporated
  3. additionthe residue is treated with a 10% KOH solution and dichloromethane
  4. customThe organic layer is dried
  5. customevaporated

Sources & evidence

ORD record
ord-23384ccff7ab4815904d29139d8d3bfa
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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