Lithium hydroxide, monohydrate → 1-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid

HRID 2191105Notes

Reaction equation

HRID 2191105 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.O[Li].O>C1COCC1.CCO.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 2

HCID 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 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 26.09 g (0.109 mol) 1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid ethyl ester in 500 mL THF, EtOH, water (1/1/1) was added 6.86 g (0.163 mol) LiOH.H2O. After 1 h at room temperature, the solvents were evaporated and the residue taken up in DCM and the organic phase was washed with aqueous HCl 1M. The organic phases were dried over Na2SO4 and evaporated under vacuum to give 19.8 g (86%) of the title compound as a white solid. MS (m/e): 212.1 [(M+H)+].

Workup

  1. customthe solvents 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 vacuum

Sources & evidence

ORD record
ord-fbf9101eed304b38b87880de96e692d1
Source dataset
uspto-grants-2012_12
Patent number
US08324248B2

Reaction notes

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