Dichloromethane ethylacetate → 2-Adamantan-1-yl-N-(2-benzyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-5-yl)-acetamide

HRID 749211Notes

Reaction equation

HRID 749211 reaction equation
[C:1]12([CH2:11][C:12]([NH:14][C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[CH:17]=[CH:18][N:19]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:20]4=[O:25])=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(Cl)Cl.CCOC(C)=O>C(O)C.[Pd]>[C:1]12([CH2:11][C:12]([NH:14][C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[CH2:17][CH2:18][N:19]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:20]4=[O:25])=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 2

HCID 21226138Dichloromethane ethylacetateHCID 250637642-Adamantan-1-yl-N-(2-benzyl-1-oxo-1,2-dihydro-isoquinolin-5-yl)-acetamide

Product 1

HCID 250637652-Adamantan-1-yl-N-(2-benzyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-5-yl)-acetamideYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 50 mL round-bottom flask was charged with a solution of 2-Adamantan-1-yl-N-(2-benzyl-1-oxo-1,2-dihydro-isoquinolin-5-yl)-acetamide (14 mg, 0.033 mmol) in absolute ethanol (6 mL) and 10% Pd/C (10 mg). The reaction vessel was evacuated and filled with hydrogen via balloon. The reaction suspension was stirred at room temperature under hydrogen (1 atm) for 17 h. The resulting mixture was filtered and the filtrate was concentrated on a rotary evaporator. The crude product was purified by prep. TLC using DCM/EtOAc (3:1) as the elutant affording the title compound (11.8 mg, 0.027 mmol, 84% yield) as a white solid.

Workup

  1. customThe reaction vessel was evacuated
  2. additionfilled with hydrogen via balloon
  3. filtrationThe resulting mixture was filtered
  4. concentrationthe filtrate was concentrated on a rotary evaporator
  5. customThe crude product was purified by prep

Sources & evidence

ORD record
ord-df051c8c7b884de0a12de4845e677ec1
Source dataset
uspto-grants-2008_07
Patent number
US07402596B2

Reaction notes

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