Trifluoroacetic acid → (S)-6-(piperidin-3-yloxy)-2H-isoquinolin-1-one

HRID 1435995Notes

Reaction equation

HRID 1435995 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21](=[O:25])[NH:20][CH:19]=[CH:18]3)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21](=[O:25])[NH:20][CH:19]=[CH:18]3)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68874974HCID 68874974, compound

Product 1

HCID 16124479(S)-6-(piperidin-3-yloxy)-2H-isoquinolin-1-oneYield 51.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-3-(Oxo-1,2-dihydroisoquinolin-6-yloxy)piperidine-1-carboxylic acid tert-butyl ester (1.25 g, 3.6 mmol) was mixed with dichloromethane (30 ml) and trifluoroacetic acid (10 ml) at ambient temperature for 15 minutes. Volatiles were removed under reduced pressure and excess trifluoroacetic acid was azeotroped with toluene. The residue was dissolved in methanol and purified using an SCX cartridge. Concentration gave (S)-6-(piperidin-3-yloxy)-2H-isoquinolin-1-one (450 mg, 51%), El-MS: m/z=245.4 [M+H]+.

Workup

  1. customVolatiles were removed under reduced pressure and excess trifluoroacetic acid
  2. customwas azeotroped with toluene
  3. dissolutionThe residue was dissolved in methanol
  4. custompurified
  5. concentrationConcentration

Sources & evidence

ORD record
ord-5293792d1d2146a8b4c4060805aec45a
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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