tert-Butyl 2-oxopiperidine-1-carboxylate → 1-Boc-4-Methylenepiperidine

HRID 2427514Notes

Reaction equation

HRID 2427514 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[C:6]([N:13]1CCC[CH2:15][C:14]1=O)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:9]([O:8][C:6]([N:13]1[CH2:14][CH2:15][C:3](=[CH2:4])[CH2:2][CH2:1]1)=[O:7])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 27568081-Boc-4-MethylenepiperidineYield 99.1%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl triphenylphosphonium bromide (5.4 g, 15.05 mmol) in THF (100 mL) was added slowly butyl lithium (2M, 15.05 mmol) at −78° C. The mixture was allowed to stir for one hour and N-Boc-piperidinone (2 g, 10.03 mmol) was added. The mixture was warmed to room temperature and stirred overnight. The THF was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over sodium sulphate, filtered and concentrated. The compound was purified by column chromatography (30% Hexanes/EtOAc) to provide the title compound (1.96 g, 99%).

Workup

  1. stirringstirred overnight
  2. customThe THF was evaporated
  3. customthe residue was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe compound was purified by column chromatography (30% Hexanes/EtOAc)

Sources & evidence

ORD record
ord-e998ce8629f643a9b9e53a85d6fbd1f7
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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