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

HRID 2287433Notes

Reaction equation

HRID 2287433 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, 2.37g) 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-0572bdc0732f4047ac39a5ccbedc7ea3
Source dataset
uspto-grants-2000_07
Patent number
US06083949

Reaction notes

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