Di-tert-butyl dicarbonate → tert-Butyl 4-oxopiperidine-1-carboxylate

HRID 2093052Notes

Reaction equation

HRID 2093052 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.C([O-])(O)=O.[Na+].[O:15](C(OC(C)(C)C)=O)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=O>O1CCOCC1.O>[C:16]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:15]

Participants

6

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 2723901Piperonylamine

Product 1

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateYield 86.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4-piperidone monohydrate hydrochloride (250 g, 1.62 mole) was dissolved in dioxane (1.5 L) and water (0.5 L). 217 g of NaHCO3 was added at 0° C. followed by slow addition of (BOC)2O (459 g, 2.1 mole). Reaction mixture was stirred for overnight. Solution was concentrated; residue was taken in water and extracted with ethyl acetate, washed with water and dried over anhydrous Na2SO4. Solvent was evaporated and product obtained was washed with hexane to get N-boc 4-piperidone (280 g).

Workup

  1. customReaction mixture
  2. concentrationSolution was concentrated
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. customSolvent was evaporated
  7. customproduct obtained
  8. washwas washed with hexane

Sources & evidence

ORD record
ord-1f3b655e24c84f958b613c29c5e99171
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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