Triacetoxyperiodinane → Tert-butyl 5-(2-(4-fluorophenyl)-6-formyl-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate

HRID 927277Notes

Reaction equation

HRID 927277 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:39]([CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([CH2:51][OH:52])[CH:36]=3)[C:31]2=[O:53])=[CH:26][CH:25]=1>ClCCl.[O-]S([O-])(=S)=O.[Na+].[Na+]>[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:39]([CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][C:47]([CH3:48])([CH3:50])[CH3:49])=[O:45])=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([CH:51]=[O:52])[CH:36]=3)[C:31]2=[O:53])=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 118558138Tert-butyl 5-(2-(4-fluorophenyl)-6-(hydroxymethyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate

Product 1

HCID 118558140Tert-butyl 5-(2-(4-fluorophenyl)-6-formyl-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoateYield 98.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24477Sodium ThiosulfateSolvent

Procedure

Dess-Martin Periodinane (1296 mg, 3.06 mmol) was added to a stirred, room temperature mixture of tert-butyl 5-(2-(4-fluorophenyl)-6-(hydroxymethyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (650 mg, 1.528 mmol) in dichloromethane (15 mL), and the mixture was stirred at room temperature for 2 h. The mixture was diluted with dichloromethane (20 mL), Na2S2O3 saturated (20 mL) was added, stirred at room temperature for 20 min, the aqueous layer was extracted once more with dichloromethane (15 mL), the combined organic was washed with aqueous sodium hydrogen carbonate saturated (3×15 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give tert-butyl 5-(2-(4-fluorophenyl)-6-formyl-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (638 mg, 1.507 mmol) as a yellow solid.

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 20 min
  3. extractionthe aqueous layer was extracted once more with dichloromethane (15 mL)
  4. washthe combined organic was washed with aqueous sodium hydrogen carbonate saturated (3×15 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-43e899c4c37546679a93e697ade3833c
Source dataset
uspto-grants-2016_03
Patent number
US09290454B2

Reaction notes

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