Tert-butyl4-(3-methyl-2-(phenylcarbamoyl)phenyl)-3-oxobutan-2-ylcarbamate → (S)-3-(1-aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one

HRID 1506101Notes

Reaction equation

HRID 1506101 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10](=O)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[C:19](=[O:27])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:9])(C)(C)C>Cl.CO>[NH2:7][C@H:8]([C:10]1[N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:19](=[O:27])[C:13]2[C:12]([CH:11]=1)=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:18])[CH3:9]

Participants

3

Reactant 1

HCID 58008575Tert-butyl4-(3-methyl-2-(phenylcarbamoyl)phenyl)-3-oxobutan-2-ylcarbamate2×

Product 1

HCID 58008747(S)-3-(1-aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

Tert-Butyl 4-(3-methyl-2-(phenylcarbamoyl)phenyl)-3-oxobutan-2-ylcarbamate (compound 4703) (4.61 g, 0.012 mol) was dissolved in HCl/MeOH (50 mL) and stirred at reflux for 30 min. The mixture was concentrated in vacuo and then saturated Na2CO3 solution was added to adjust PH to about 7-8. The resulting solid was collected by filtration and further dried in vacuo to afford the desired product, 3-(1-aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (compound 4704) (2.9 g, 90% yield, where the ratio of isomers is S:R=5:1) as a white solid.

Workup

  1. temperatureat reflux for 30 min
  2. concentrationThe mixture was concentrated in vacuo
  3. additionsaturated Na2CO3 solution was added
  4. filtrationThe resulting solid was collected by filtration
  5. customfurther dried in vacuo

Sources & evidence

ORD record
ord-90d53767ba5c4116ab7912a3c5fa0409
Source dataset
uspto-grants-2015_12
Patent number
US09216982B2

Reaction notes

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