Methyl iodide → 1-tert-Butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate

HRID 862202Notes

Reaction equation

HRID 862202 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[CH2:13]([O:15][C:16](=[O:30])[CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1)[CH3:14].CI>C1COCC1.C(OCC)(=O)C>[CH2:13]([O:15][C:16](=[O:30])[C:17]1([CH3:1])[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]1)[CH3:14]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylateHCID 178418339Butyllithium

Product 1

HCID 162182761-tert-Butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylateYield 105%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of diisopropylamine (20.0 mmol, 2.02 g) in THF (50 mL) cooled to -78° C. was added n-butyllithium (21.7 mmol, 8.68 mL of a 2.5M solution in hexanes). N-tert-butoxycarbonyl isonipecotic acid ethyl ester (16.7 mmol, 4.5 g) was then added dropwise followed by methyl iodide (16.7 mmol, 2.37 g)and the reaction allowed to warm to room temperature. The mixture was then diluted with ethyl acetate (500 mL) and washed with water (1×200 mL), 10% KHSO4 (200 mL) and brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to give 4.76 g of the title compound as a pale yellow oil.

Workup

  1. washwashed with water (1×200 mL), 10% KHSO4 (200 mL) and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ab6774ca427942348b8db0d3699ec6fe
Source dataset
uspto-grants-1998_02
Patent number
US05717100

Reaction notes

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