Bromide ion → tert-Butyl 4-(bromomethylidene)piperidine-1-carboxylate

HRID 1895969Notes

Reaction equation

HRID 1895969 reaction equation
[Li].[Br-:2].[C:3]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=O)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH2:17]1COCC1>>[Br:2][CH:17]=[C:13]1[CH2:14][CH2:15][N:10]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH2:11][CH2:12]1

Participants

5

Reactant 4

HCID 259Bromide ionHCID 8028TetrahydrofuranHCID 3028194LithiumHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylate

Product 1

HCID 45489892tert-Butyl 4-(bromomethylidene)piperidine-1-carboxylate

Procedure

Lithium bis-trimethylsylylamide (1 M in THF, 7.38 mL, 7.38 mmol) was dropped into a suspension of bromomethyltriphenylphsphonium bromide (3.22 g, 7.38 mmol) at −15° C. under nitrogen atmosphere. After 15 min. under stirring at the same temperature, N-Boc piperidone (1.4 g, 7.03 mmol) dissolved in THF (10 ml) was added. Stirring was maintained and after 2 h at r.t., the reaction mixture was quenched with water and with EtOAc. The combined extracts were washed, dried over Na2SO4 and evaporated to dryness. The crude residue was purified by flash chromatography (EtOAc—Petroleum Ether 98:2) affording the title product (1.27 g).

Workup

  1. additionwas added
  2. customthe reaction mixture was quenched with water and with EtOAc
  3. washThe combined extracts were washed
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude residue was purified by flash chromatography (EtOAc—Petroleum Ether 98:2)

Sources & evidence

ORD record
ord-d3d3b2e6c92d4778b1ca41ec0c2e60ac
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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