tert-Butyl 4-oxopiperidine-1-carboxylate → 5-Tert-butyl 2-ethyl 6,7-dihydro-1H-pyrrolo[3,2-C]pyridine-2,5(4H)-dicarboxylate

HRID 2093094Notes

Reaction equation

HRID 2093094 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([N-:18]C(C)C)(C)C.[Li+].[C:23]([O:28][CH2:29][CH2:30]Br)(=[O:27])[C:24]([CH3:26])=O>C1COCC1>[NH:18]1[C:11]2[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][C:10]=2[CH:26]=[C:24]1[C:23]([O:28][CH2:29][CH3:30])=[O:27]

Participants

5

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724682Lithium diisopropylamideHCID 86587973Bromoethyl pyruvate

Product 1

HCID 668643095-Tert-butyl 2-ethyl 6,7-dihydro-1H-pyrrolo[3,2-C]pyridine-2,5(4H)-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-boc-4-piperidone (1 eq.) and lithium di-isopropyl amide (1 eq.) in THF was stirred at −78° C. and for 2 hrs. A bromoethyl pyruvate (1.2 eq.) was added to above reaction mixture and stirred for 30 min. Reaction mixture was then quenched with ammonia solution and then extracted with ethyl acetate, dried over sodium sulphate and concentrated to dryness. The residue was then dissolved in dichoromethane and was added silica (100-200 mesh), stirred for overnight at room temperature. Crude was then purified by silica gel column chromatography to yield 5-tert-butyl 2-ethyl 1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridine-2,5-dicarboxylate.

Workup

  1. customReaction mixture
  2. customwas then quenched with ammonia solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated to dryness
  6. dissolutionThe residue was then dissolved in dichoromethane
  7. additionwas added silica (100-200 mesh)
  8. stirringstirred for overnight at room temperature
  9. customCrude was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6f708db8a9684e74b0489fe18c279fe5
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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