Bromine → 1-tert-Butyloxycarbonyl-3-bromo-4-oxopiperidine

HRID 1358923Notes

Reaction equation

HRID 1358923 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:15]Br>C1COCC1.CCOCC.C(OCC)(=O)C.[Cl-].[Al+3].[Cl-].[Cl-]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[O:14])[CH:12]([Br:15])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 2

HCID 24408BromineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 106839701-tert-Butyloxycarbonyl-3-bromo-4-oxopiperidineYield 43%

Reagents, catalysts & solvents 4

HCID 6451240Aluminum(III) ChlorideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-tert-Butoxycarbonyl-4-piperidone (5.67 g, 28.5 mol) is dissolved in a mixture of dry THF (50 ml) and dry ether (50 ml), and thereto is added anhydrous aluminum chloride (57 mg). To the mixture is gradually added dropwise bromine (1.47 ml, 28.5 mmol) at 0° C., and the mixture is allowed to stand at 5° C. for 24 hours. The resulting reaction solution is diluted with ethyl acetate, and the mixture is washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and the solvent is evaporated. The resulting residue is crystallized from ether to give N-tert-butoxycarbonyl-3-bromo-4-piperidone (3.40 g, yield; 43%) as pale yellow crystals.

Workup

  1. customThe resulting reaction solution
  2. washthe mixture is washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated
  5. customThe resulting residue is crystallized from ether

Sources & evidence

ORD record
ord-66ed7b8919e04cddbc0148dc9357e63b
Source dataset
uspto-grants-2003_07
Patent number
US06599895B1

Reaction notes

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