Hydrofluoric Acid → 4-Hydroxy-piperidine-1-carboxylic Acid 5-benzoylamino-pyridin-2-yl Ester

HRID 1179938Notes

Reaction equation

HRID 1179938 reaction equation
F.[C:2]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]([N:20]2[CH2:25][CH2:24][CH:23]([O:26][Si](C(C)(C)C)(C)C)[CH2:22][CH2:21]2)=[O:19])=[N:15][CH:16]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(#N)C>[C:2]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]([N:20]2[CH2:21][CH2:22][CH:23]([OH:26])[CH2:24][CH2:25]2)=[O:19])=[N:15][CH:16]=1)(=[O:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14917Hydrofluoric AcidHCID 695176994-(tert-Butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic Acid 5-benzoylamino-pyridin-2-yl Ester

Product 1

HCID 695177674-Hydroxy-piperidine-1-carboxylic Acid 5-benzoylamino-pyridin-2-yl EsterYield 68.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

hydrofluoric acid (min. 40% in water, 0.50 mL) was added to a stirred solution of 4-(tert-butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic acid 5-benzoylamino-pyridin-2-yl ester (364 mg, 0.77 mmol) in acetonitrile. After stirring overnight at room temperature the solvent was evaporated in vacuo. The residue was redissolved in dichloromethane. After addition of triethylamine (1 mL) the solution was filtered over a short pad of silicagel and washed with ethyl acetate:acetone 50:50. Evaporation of the solvent yielded the title compound (180 mg, 68% yield) as a white solid.

Workup

  1. customwas evaporated in vacuo
  2. dissolutionThe residue was redissolved in dichloromethane
  3. additionAfter addition of triethylamine (1 mL) the solution
  4. filtrationwas filtered over a short pad of silicagel
  5. washwashed with ethyl acetate:acetone 50:50
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ccd7a232f8594d4883fa26e928082311
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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