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

HRID 390168Notes

Reaction equation

HRID 390168 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 58295682(E)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxylic acidYield 144.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f55850f79be5430fb0cca250ad9e7ea0
Source dataset
uspto-grants-2013_02
Patent number
US08383629B2

Reaction notes

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