Ethanol → (R)-2-(3-Fluoro-4-(trifluoromethyl)phenyl)-N-(2-(1-hydroxypropan-2-yl)-6-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-5-yl)acetamide

HRID 1161301Notes

Reaction equation

HRID 1161301 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([NH:15][C:16]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][N:20]([C@H:28]([CH3:31])[CH2:29][OH:30])[C:21]3=[O:27])=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C(O)C>[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([NH:15][C:16]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[C:17]=2[CH2:18][CH2:19][N:20]([C@H:28]([CH3:31])[CH2:29][OH:30])[C:21]3=[O:27])=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10]

Participants

4

Reactant 2

HCID 702EthanolHCID 25013922(R)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(2-(1-hydroxypropan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

Product 1

HCID 52912999(R)-2-(3-Fluoro-4-(trifluoromethyl)phenyl)-N-(2-(1-hydroxypropan-2-yl)-6-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-5-yl)acetamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A round bottom flask was charged with (R)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(2-(1-hydroxypropan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide (50.0 mg, 0.000114 mol), ethanol (6 mL, 0.1 mol) and palladium, 10% weight on charcoal (1.4 mg, 0.000011 mol) was added and the flask was evacuated and flushes with hydrogen. The evacuation and flushing was repeated two times and the reaction was stirred under an atmosphere of hydrogen (balloon) over night. The reaction mixture was then filtered over cellite and solvent removed under reduced pressure. The residue was then purified by flash chromatography to get the product as white solid.

Workup

  1. additionwas added
  2. customthe flask was evacuated
  3. customThe evacuation and flushing
  4. filtrationThe reaction mixture was then filtered over cellite and solvent
  5. customremoved under reduced pressure
  6. customThe residue was then purified by flash chromatography

Sources & evidence

ORD record
ord-199e4788ccc1414cbfd341656327ebae
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

Loading…