Lithium diisopropylamide → Ethyl 4-methylpiperidine-4-carboxylate

HRID 2289551Notes

Reaction equation

HRID 2289551 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[CH:22]([N-]C(C)C)(C)C.[Li+]>C1COCC1.C(OCC)(=O)C.O>[CH3:22][C:14]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1

Participants

6

Reactant 2

HCID 2724682Lithium diisopropylamideHCID 152896721-Benzyl 4-ethyl piperidine-1,4-dicarboxylate

Product 1

HCID 19361805Ethyl 4-methylpiperidine-4-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-Methyl-4-ethoxycarbonyl-piperidine was prepared by alkylation of 1-(benzyloxycarbonyl)-4-ethoxycarbonyl-piperidine (J.Med.Chem 1994, 37, p 368)-2.6 g (10 mmol) 1. in 25 ml dry THF at -70° C., under argon, treated with 7 ml lithium di-isopropylamide solution (2M). Stirred 1.5 hours then a solution of 1.5 equivalents of alkyl halide in 5 ml of THF added dropwise. Reaction allowed to warm to ambient temperature over several hours, diluted with ethyl acetate and water. Aqueous layer extracted twice with ethyl acetate, organic solution washed with brine and dried. Evaporated to give the liquid product.

Workup

  1. customReaction
  2. extractionAqueous layer extracted twice with ethyl acetate, organic solution
  3. washwashed with brine
  4. customdried
  5. customEvaporated
  6. customto give the liquid product

Sources & evidence

ORD record
ord-ebee02998eeb43ceb7df329971dd7d51
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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