HCID 59216509, compound → HCID 59216428, compound

HRID 2069823Notes

Reaction equation

HRID 2069823 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

Conditions

Temperature
80 °C

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 Mg504 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. concentrationThe reaction was concentrated to dryness
  2. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  3. customseparated layers
  4. washwashed ethyl acetate with brine
  5. customdried Mg504
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c8675c611a064293848ebec42509dadd
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

Loading…