Ethanol → 1-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid

HRID 559313Notes

Reaction equation

HRID 559313 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([C:14]2([CH3:17])[CH2:16][CH2:15]2)=[O:13])[CH2:8][CH2:7]1)=[O:5])C.C1COCC1.CCO.O[Li].O>O>[CH3:17][C:14]1([C:12]([N:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)=[O:13])[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 594381441-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 594381681-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 1-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid ethyl ester (26.09 g, 0.109 mol) in 500 mL of a mixture of THF, EtOH and H2O) (1/1/1) was added LiOH.H2O) (6.86 g, 0.163 mol). After one hour at RT, the solvent were evaporated and the residue taken up in CH2Cl2 and the organic phase was washed with aqueous HCl 1M. The organic phases were dried over Na2SO4 and evaporated under vacuo to gave 19.8 g (86%) of the title compound as a white solid. ES-MS m/e: 212.1 (M+H+).

Workup

  1. customthe solvent were evaporated
  2. washthe organic phase was washed with aqueous HCl 1M
  3. dry with materialThe organic phases were dried over Na2SO4
  4. customevaporated under vacuo

Sources & evidence

ORD record
ord-8a46a28ed8eb40548393ec1d7237d4cc
Source dataset
uspto-grants-2011_11
Patent number
US08063075B2

Reaction notes

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