Lithium hydroxide, monohydrate → HCID 58171834, compound

HRID 1891331Notes

Reaction equation

HRID 1891331 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:13]=[N:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[CH2:8][CH2:7]1)=[O:5])C.O[Li].O>C1COCC1.O.CO>[CH3:19][O:18][C:15]1[N:14]=[N:13][C:12]([N:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58303086HCID 58303086, compound

Product 1

HCID 58171834HCID 58171834, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution 1-(6-methoxy-pyridazin-3-yl)-piperidine-4-carboxylic acid ethyl ester (3.20 g, 12.06 mmol) in THF (40 mL), H2O (40 mL) and MeOH (4 mL) was added LiOH.H2O (600 mg, 14.3 mmol). Stirring was continued overnight at RT before the organic solvent were removed under vacuo. The pH of the was adjusted to 5 with acetic acid, and the product extracted with EtOAc, dried over Na2SO4. The resulting solid was suspended in heptane, filtered off, washed with cold Et2O to give 1.48 g (61%) of 1-(6-methoxy-pyridazin-3-yl)-piperidine-4-carboxylic acid. ES-MS m/e: 236.2 (M−H+)

Workup

  1. customwere removed under vacuo
  2. extractionthe product extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered off
  5. washwashed with cold Et2O

Sources & evidence

ORD record
ord-0483858ea3c9454e857d8554462acec0
Source dataset
uspto-grants-2013_08
Patent number
US08507535B2

Reaction notes

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