Sodium Hydroxide → HCID 67491593, compound

HRID 537090Notes

Reaction equation

HRID 537090 reaction equation
[Br:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[CH2:11][C:12]1([C:25]([O:27]CC)=[O:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.[OH-].[Na+]>CO>[Br:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[CH2:11][C:12]1([C:25]([OH:27])=[O:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 674915481,4-Piperidinedicarboxylic acid, 4-[[5-bromo-1-(1,1-dimethylethyl)-1H-pyrazol-4-yl]methyl]-, 1-(1,1-dimethylethyl) 4-ethyl ester

Product 1

HCID 67491593HCID 67491593, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-tert-butyl 4-ethyl 4-((5-bromo-1-tert-butyl-1H-pyrazol-4-yl)methyl)piperidine-1,4-dicarboxylate (256 mg, 0.54 mmol) in methanol (15 mL) was added aqueous 2.5 M NaOH (5 mL), and the resultant mixture was heated at reflux for 18 hours. The mixture was cooled to room temperature and methanol was removed under reduced pressure. The resultant slurry was taken up in 25 mL water, acidified with aqueous 1 N HCl, and then extracted with ethyl acetate (2×50 mL). The combined organics were dried over sodium sulfate, filtered and concentrated to yield 241 mg of 4-((5-bromo-1-tert-butyl-1H-pyrazol-4-yl)methyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid as a colorless solid. +APCI (M+H) 444.2, (M+2+H) 446.2; 1H NMR (400 MHz, CDCl3, δ): 7.35 (s, 1H), 3.95 (br. s., 2H), 2.92 (br. s., 2H), 2.71 (s, 2H), 2.08 (d, J=12.9 Hz, 2H), 1.73 (s, 9H), 1.50 (m, 11H).

Workup

  1. temperatureat reflux for 18 hours
  2. custommethanol was removed under reduced pressure
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-88bd9dd8107a48af97933048c8710b2c
Source dataset
uspto-grants-2014_10
Patent number
US08859773B2

Reaction notes

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