Acetic Acid → Ethyl 1-isopropylpiperidine-4-carboxylate

HRID 30784Notes

Reaction equation

HRID 30784 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:12][C:13]([CH3:15])=O.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH:13]([CH3:15])[CH3:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 70770Ethyl 4-piperidinecarboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19900430Ethyl 1-isopropylpiperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To ethylpiperidine-4-carboxylate (1 eq) in methanol was added acetone (1 eq) and acetic acid (5%) and the resulting mixture was stirred for 2 h at ambient temperature. To it was then added sodium cyanoborohydride (1 eq) and continued stirring for 16 h. The mixture was then concentrated and to it was added sodium bicarbonate and was partitioned between ethyl acetate and water. The organic layer was dried with sodium sulfate and concentrated to yield ethyl-1-(methylethyl)piperidine-4-carboxylate. To this was then added concentrated hydrochloric acid and water (2:1) and the mixture was refluxed for 5 h. The resulting 1-(methylethyl)piperidine-4-carboxylic acid was then azeotroped with toluene. MS: MH+=172.

Workup

  1. concentrationThe mixture was then concentrated and to it
  2. additionwas added sodium bicarbonate
  3. customwas partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0b6602ef88014232997f539687d070ce
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Reaction notes

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