Methyl iodide → (E)-methyl 1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxylate

HRID 390167

Reaktionsgleichung

Reaktionsgleichung von HRID 390167
[O:1]=[C:2]1[C:10]2([CH2:15][CH2:14][N:13]([C:16](=[O:29])/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])[CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:30]([O:32][CH3:33])=[O:31])[CH:8]=2)[NH:3]1.[H-].[Na+].[CH3:36]I>C1COCC1>[CH3:36][N:3]1[C:4]2[C:9](=[CH:8][C:7]([C:30]([O:32][CH3:33])=[O:31])=[CH:6][CH:5]=2)[C:10]2([CH2:15][CH2:14][N:13]([C:16](=[O:29])/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:26])([F:27])[F:28])[CH2:12][CH2:11]2)[C:2]1=[O:1]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58295691(E)-methyl 2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxylate

Produkt 1

HCID 44226871(E)-methyl 1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxylateAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of (E)-methyl 2-oxo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4′-piperidine]-5-carboxylate (150 mg, 0.33 mmol) in THF (3 mL) was added to a suspension of NaH (27 mg, 0.66 mmol) in THF at 0° C. and stirred for 30 min at the same temperature. Methyl iodide (58 mg, 0.41 mmol) was added to the above mixture. The reaction mixture was stirred at rt for 2 h. The reaction mixture was poured into ice water and extracted with EtOAc (2×50 mL). The combined organic phases were dried over NaSO4, filtered and concentrated to give (E)-methyl 1-methyl-2-oxo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4′-piperidine]-5-carboxylate (90 mg, 58%). 1H NMR (CD3OD): 1.85-2.02 (m, 4H), 3.26 (s, 3H), 3.88 (s, 3H), 3.95 (m, 1H), 4.15 (m, 1H), 4.28 (m, 1H), 7.10 (m, 1H), 7.26 (m, 1H), 7.52 (m, 1H), 7.68 (m, 1H), 7.77 (m, 1H), 8.06 (m, 4H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at rt for 2 h
  2. extractionextracted with EtOAc (2×50 mL)
  3. dry with materialThe combined organic phases were dried over NaSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-84b61d96a56543f4b89782f225e0e673
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383629B2

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