Acetic Acid → HCID 28411268, compound

HRID 1747499Notes

Reaction equation

HRID 1747499 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)#[N:9].C(O)(=O)C>C1COCC1.CO>[C:8]([C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH2:17][CH2:18][CH:19]([C:22]([O:24][CH3:1])=[O:23])[CH2:20][CH2:21]2)=[CH:14][CH:15]=1)#[N:9]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 193914381-(4-Cyanophenyl)piperidine-4-carboxylic acid

Product 1

HCID 28411268HCID 28411268, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(Trimethylsilyl)diazomethane (2.0 M solution in hexane, 2.7 mL, 5.40 mmol) was added to a mixed solution of 1-(4-cyanophenyl)piperidine-4-carboxylic acid (1.13 g, 4.91 mmol) in THF (13 mL) and methanol (6.5 mL) (2:1, v/v), and the mixture was stirred at room temperature for 1 hour. Acetic acid (appropriate amount) was added to the reaction solution to stop the reaction. Then, the solvent was distilled off under reduced pressure. A saturated sodium bicarbonate aqueous solution was added to the obtained residue, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=80/20] to obtain the title compound (1.06 g, yield: 88%).

Workup

  1. customthe reaction
  2. distillationThen, the solvent was distilled off under reduced pressure
  3. additionA saturated sodium bicarbonate aqueous solution was added to the obtained residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe obtained organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=80/20]

Sources & evidence

ORD record
ord-c200717730ae420caf0c51a7259931ad
Source dataset
uspto-grants-2015_10
Patent number
US09150575B2

Reaction notes

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