Bromide ion → 1-Boc-4-Methylenepiperidine

HRID 2300174Notes

Reaction equation

HRID 2300174 reaction equation
[Br-].O=[C:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[C:16](O[K])(C)(C)C>O1CCCC1>[CH2:16]=[C:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 259Bromide ionHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178418922HCID 178418922, compound

Product 1

HCID 27568081-Boc-4-MethylenepiperidineYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

47.2 g of methyltoluphenylphosphonium bromide and 21.9 g of tert-butyl 4-oxo-1-piperidinecarboxylate were added to a mixture of 14.8 g tert-butoxy potassium and 300 ml tetrahydrofuran, and stirred for 40 min at room temperature. The reaction solution was evaporated, diethyl ether was added thereto, and then filtered through Celite. The filtrate was washed with water and brine; dried over anhydrous magnesium sulfate, and then filtered. The filtrate was evaporated, and the resulting residue was subjected to silica gel column chromatography to give 20.8 g of tert-butyl 4-methylene-1-piperidinecarboxylate.

Workup

  1. customThe reaction solution was evaporated
  2. additiondiethyl ether was added
  3. filtrationfiltered through Celite
  4. washThe filtrate was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b3aa0b5ec24749f7bf4c856da5510fa3
Source dataset
uspto-grants-2002_12
Patent number
US06498159B1

Reaction notes

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