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

HRID 566409Notes

Reaction equation

HRID 566409 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)[CH3:2].[CH:19]([N-]C(C)C)(C)[CH3:20].[Li+].C(I)C.O>C1COCC1>[CH2:1]([O:3][C:4](=[O:18])[C:5]1([CH2:19][CH3:20])[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 2724682Lithium diisopropylamideHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Product 1

HCID 53393415Ethyl 1-Boc-4-ethyl-4-piperidine carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-tert-butoxycarbonylisonipecotic acid ethyl ester (576 mg) in THF (15 ml) was added a solution of lithium diisopropyl-amide (290 mg) in THF (10 ml) in a stream of argon gas at −78° C., and the reaction mixture was stirred at the same temperature for 1 hour. Ethyl iodide (0.36 ml) was added to the above solution at −78° C., and the mixture was stirred for 18 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 1N hydrochloric acid, water and saturated brine, and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to give the title compound (585 mg, yield 92%).

Workup

  1. stirringthe mixture was stirred for 18 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with 1N hydrochloric acid, water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1daa4b681db447b596278e5e5f66bf13
Source dataset
uspto-grants-2001_01
Patent number
US06174887B1

Reaction notes

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