Hydrochloric Acid → Tert-butyl 2-(4-fluorophenyl)-6-oxopiperidin-1-ylcarbamate

HRID 599581Notes

Reaction equation

HRID 599581 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][NH:11][CH:12]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH2:13][CH2:14][CH2:15][C:16](OC)=[O:17])=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl>CO>[C:3]([O:7][C:8](=[O:9])[NH:10][N:11]1[C:16](=[O:17])[CH2:15][CH2:14][CH2:13][CH:12]1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67067136methyl 5-(N'-tert-butoxycarbonylhydrazino)-5-(4-fluorophenyl)pentanoate

Product 1

HCID 66859411Tert-butyl 2-(4-fluorophenyl)-6-oxopiperidin-1-ylcarbamateYield 68.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 N sodium hydroxide solution (0.6 mL) was added to a solution of methyl 5-(N′-tert-butoxycarbonylhydrazino)-5-(4-fluorophenyl)pentanoate (81 mg) in methanol (1 mL), and the reaction solution was stirred at room temperature for two hours. 2 N aqueous hydrochloric acid (0.3 mL) was added to the reaction solution, and the reaction solution was concentrated under reduced pressure. HOBT (64 mg) and EDC (91 mg) were added to a solution of the residue in DMF (1 mL), and the reaction solution was stirred at room temperature for two hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=9:1→ethyl acetate) to obtain 50 mg of the title compound. The property values of the compound are as follows.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. additionHOBT (64 mg) and EDC (91 mg) were added to a solution of the residue in DMF (1 mL)
  3. stirringthe reaction solution was stirred at room temperature for two hours
  4. additionEthyl acetate and saturated sodium bicarbonate water were added to the reaction solution
  5. customthe organic layer was separated
  6. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=9:1→ethyl acetate)

Sources & evidence

ORD record
ord-83d33c64b476494dac961dab11b669f1
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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