Acetic Acid → Ethyl 1-isopropylpiperidine-4-carboxylate

HRID 1963702Notes

Reaction equation

HRID 1963702 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-bb54a7b705c44f6fade2080d09478663
Source dataset
uspto-grants-2013_04
Patent number
US08415382B2

Reaction notes

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