Trifluoroacetic acid → (E)-Ethyl 3-(2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4'-piperidine]-6-yl)acrylate

HRID 83003Notes

Reaction equation

HRID 83003 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11](=[O:37])/[CH:12]=[CH:13]/[C:14]1[CH:15]=[C:16]2[C:33](=[N:34][CH:35]=1)[NH:32][C:31](=[O:36])[C:18]1([CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]1)[CH2:17]2)[CH3:9]>ClCCl>[O:36]=[C:31]1[C:18]2([CH2:19][CH2:20][NH:21][CH2:22][CH2:23]2)[CH2:17][C:16]2[C:33](=[N:34][CH:35]=[C:14](/[CH:13]=[CH:12]/[C:11]([O:10][CH2:8][CH3:9])=[O:37])[CH:15]=2)[NH:32]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67154730(E)-tert-Butyl 6-(3-ethoxy-3-oxoprop-1-enyl)-2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4'-piperidine]-1'-carboxylate

Product 1

HCID 68338146(E)-Ethyl 3-(2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4'-piperidine]-6-yl)acrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to a suspension of (E)-tert-butyl 6-(3-ethoxy-3-oxoprop-1-enyl)-2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-1′-carboxylate (1.52 g, 3.66 mmol) in dichloromethane (20 mL). The reaction mixture was stirred at room temperature for 1 hour and concentrated to dryness. The resulting residue was partitioned between an aqueous solution of sodium hydroxide (1N, 60 mL) and dichloromethane (40 mL). The aqueous layer was separated and extracted with dichloromethane (2×70 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated to dryness. The title product was obtained as a pale yellow solid (904 mg, 79%).

Workup

  1. concentrationconcentrated to dryness
  2. customThe resulting residue was partitioned between an aqueous solution of sodium hydroxide (1N, 60 mL) and dichloromethane (40 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with dichloromethane (2×70 mL)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2540b885f84d4c2f8ae76ca1def8b818
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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