Ethyl Acetate → HCID 117701764, compound

HRID 1507453Notes

Reaction equation

HRID 1507453 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([CH:19]=[O:20])=[C:17]2[C:12]([C:13](=[O:38])[C:14]([CH3:37])=[C:15]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:28])[CH2:23][CH2:22]3)[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[C:41]([F:44])([F:43])[F:42].C(OCC)(=O)C>CS(C)=O>[CH2:1]([O:8][C:9]1[C:18]([CH:19]([OH:20])[C:41]([F:44])([F:43])[F:42])=[C:17]2[C:12]([C:13](=[O:38])[C:14]([CH3:37])=[C:15]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)=[O:28])[CH2:23][CH2:22]3)[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 117701569HCID 117701569, compound

Product 1

HCID 117701764HCID 117701764, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of benzyl 4-[7-(benzyloxy)-8-formyl-3-methyl-4-oxo-4H-chromen-2-yl]piperidine-1-carboxylate (378 mg, 0.74 mmol) obtained in Example 36-1 in dimethyl sulfoxide (10 mL), molecular sieves 4A (1.0 g) and trimethyl(trifluoromethyl)silane (1.09 mL, 7.39 mmol) were added, and then the mixture was stirred at room temperature for 3 hours. Ethyl acetate (80 mL) was added to the reaction solution, and insoluble matter was removed by filtration through celite. The filtrate was washed with water and then dried over sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. A 1 N aqueous hydrochloric acid solution (3 mL) and methanol (12 mL) were added to the obtained residue, and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the obtained residue. The organic layer was washed with water and then dried over sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=80/20→40/60) to obtain 392 mg of the title compound (yield: 91%).

Workup

  1. customwas removed by filtration through celite
  2. washThe filtrate was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionA 1 N aqueous hydrochloric acid solution (3 mL) and methanol (12 mL) were added to the obtained residue
  7. stirringthe mixture was stirred at room temperature for 2 hours
  8. concentrationThe reaction solution was concentrated under reduced pressure, and ethyl acetate
  9. additionwas added to the obtained residue
  10. washThe organic layer was washed with water
  11. dry with materialdried over sodium sulfate
  12. filtrationThe desiccant was filtered off
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=80/20→40/60)

Sources & evidence

ORD record
ord-0c61b08e308143508a07a74d77ddf13e
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

Loading…