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

HRID 2093053Notes

Reaction equation

HRID 2093053 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:15]Br>ClCCl>[C:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([Br:15])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 106839701-tert-Butyloxycarbonyl-3-bromo-4-oxopiperidineYield 32.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-boc-4-piperidone (100 gm, 0.5 mole) obtained in step H1 was dissolved in 4.0 L of dichloromethane. Bromine (96.3 gm, 0.6 mole) in 100 ml of dichloromethane was added at room temperature under stirring and nitrogen bubbling. After completion of bromine addition, the reaction mixture was stirred further at room temperature for additional 30 minutes and then filtered. Filtrate was concentrated and crystallized by dichloromethane/petroleum ether to get the product N-boc-3-bromo-4-piperidone (45.0 gm).

Workup

  1. stirringthe reaction mixture was stirred further at room temperature for additional 30 minutes
  2. filtrationfiltered
  3. concentrationFiltrate was concentrated
  4. customcrystallized by dichloromethane/petroleum ether

Sources & evidence

ORD record
ord-e8a525e9e3654d8ca68bfcf1722d7603
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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