Iodoethane → Ethyl 1-Boc-4-ethyl-4-piperidine carboxylate

HRID 333427Notes

Reaction equation

HRID 333427 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH:19]([N-]C(C)C)(C)[CH3:20].[Li+].ICC.[Cl-].[NH4+]>C1COCC1>[CH2:19]([C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:8][CH2:7]1)[CH3:20]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Product 1

HCID 53393415Ethyl 1-Boc-4-ethyl-4-piperidine carboxylateYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.2 g (0.78 mmol) of tert-butyl 4-ethoxycarbonylpiperidine-1-carboxylate is dissolved in 4 mL of THF at −10° C. 0.8 mL (1.56 mmol) of lithium diisopropylamide is added dropwise. After 15 minutes, 0.09 mL (1.2 mmol) of iodoethane is added and the mixture is warmed to room temperature. It is stirred for 30 minutes and then poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase is dried and then concentrated to dryness. The oil obtained is chromatographed on silica gel (eluent: 95/5 heptane/ethyl acetate). 183 mg of tert-butyl 4-ethyl-4-ethoxycarbonylpiperidine-1-carboxylate in the form of a yellow oil are obtained in a yield of 82%.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is dried
  3. concentrationconcentrated to dryness
  4. customThe oil obtained
  5. customis chromatographed on silica gel (eluent: 95/5 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-c0d67e2194f64c37a95bbd3bcda12e8d
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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