HCID 59216509, compound → HCID 59216428, compound

HRID 2245722Notes

Reaction equation

HRID 2245722 reaction equation
[CH3:1][C:2]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[N:20](CC1C=CC(OC)=CC=1)[CH2:19][CH2:18]2)([CH3:14])[CH2:3][O:4][CH2:5][CH2:6][O:7]C1CCCCO1>FC(F)(F)C(O)=O>[OH:7][CH2:6][CH2:5][O:4][CH2:3][C:2]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[NH:20][CH2:19][CH2:18]2)([CH3:14])[CH3:1]

Participants

3

Reactant 1

HCID 59216509HCID 59216509, compound

Product 1

HCID 59216428HCID 59216428, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

140 mg 6-{1,1-Dimethyl-2-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-ethyl}-2-(4-methoxy-benzyl)-3,4-dihydro-2H-isoquinolin-1-one (0.3 mmol, 1 eq) was dissolved in 5 ml trifluoroacetic acid, and the mixture heated to 80 C for 16 hours. The reaction was concentrated to dryness, partitioned between ethyl acetate and saturated sodium bicarbonate, separated layers and washed ethyl acetate with brine, dried MgSO4 and concentrated to give 75 mg 6-[2-(2-Hydroxy-ethoxy)-1,1-dimethyl-ethyl]-3,4-dihydro-2H-isoquinolin-1-one, M+H=264 which was used without purification in the next step.

Workup

  1. temperaturethe mixture heated to 80 C for 16 hours
  2. concentrationThe reaction was concentrated to dryness
  3. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  4. customseparated layers
  5. washwashed ethyl acetate with brine, dried MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a32e4a043a844b39a141333b74532d03
Source dataset
uspto-grants-2010_03
Patent number
US07683064B2

Reaction notes

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