Lithium Hydroxide → (E)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxylic acid

HRID 390168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390168
[CH3:1][N:2]1[C:29]2[C:24](=[CH:25][C:26]([C:30]([O:32]C)=[O:31])=[CH:27][CH:28]=2)[C:4]2([CH2:9][CH2:8][N:7]([C:10](=[O:23])/[CH:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[CH2:6][CH2:5]2)[C:3]1=[O:34].[Li+].[OH-]>CO.O>[CH3:1][N:2]1[C:29]2[C:24](=[CH:25][C:26]([C:30]([OH:32])=[O:31])=[CH:27][CH:28]=2)[C:4]2([CH2:9][CH2:8][N:7]([C:10](=[O:23])/[CH:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:20])[F:21])[CH2:6][CH2:5]2)[C:3]1=[O:34]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 44226871(E)-methyl 1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxylate

Produkt 1

HCID 58295682(E)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxylic acidAusbeute 144,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of (E)-methyl 1-methyl-2-oxo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4′-piperidine]-5-carboxylate (75 mg, 0.16 mmol) in methanol (4 mL) was added a solution of LiOH in H2O (2 M, 4 mL) at rt and the mixture was stirred for 8 h at rt. The reaction mixture was concentrated to remove methanol and extracted with CH2Cl2 twice. The combined organic phases were dried, filtered and concentrated to give (E)-1-methyl-2-oxo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4′-piperidine]-5-carboxylic acid (106 mg, 65%). 1H NMR (CD3OD): 1.94 (m, 4H), 3.26 (s, 3H), 4.15 (m, 3H), 4.22 (m, 1H), 7.01 (d, 1H), 7.28 (d, 1H), 7.53 (m, 1H), 7.66 (m, 1H), 7.76 (m, 1H), 8.01 (m, 3H), 8.08 (m, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto remove methanol
  3. extractionextracted with CH2Cl2 twice
  4. customThe combined organic phases were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f55850f79be5430fb0cca250ad9e7ea0
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383629B2

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