tert-Butyl 4-oxopiperidine-1-carboxylate → 1-Boc-4-Methylenepiperidine

HRID 1749964Notes

Reaction equation

HRID 1749964 reaction equation
[C:1](O[K])(C)(C)C.O=[C:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCCCCC>[CH2:1]=[C:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1

Participants

5

Reactant 2

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

Product 1

HCID 27568081-Boc-4-MethylenepiperidineYield 67.1%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8058HexaneSolvent

Procedure

A solution of methyltriphenylphosphonium bromide (2.15 g, 6.02 mmol) in hexane (15 mL) was added with tert-butoxypotassium (0.676 g, 6.02 mmol), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added portionwise with tert-butyl 4-oxopiperidine-1-carboxylate (1.10 g, 5.52 mmol), and the mixture was stirred overnight at room temperature. The solid was removed by filtration, the concentrated filtrate was added with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl 4-methylenepiperidine-1-carboxylate (0.731 g, 67%).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe solid was removed by filtration
  3. additionthe concentrated filtrate was added with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-013cb2b78ee5490c9d1ca9fc11f0f2e2
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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