Lithium hydroxide, monohydrate → 1-(5-Fluoropyridin-2-yl)piperidine-4-carboxylic acid

HRID 1891327Notes

Reaction equation

HRID 1891327 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])C.O[Li].O>C1COCC1.O.CO>[F:18][C:15]1[CH:16]=[CH:17][C:12]([N:9]2[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)=[N:13][CH:14]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58302994Ethyl 1-(5-fluoropyridin-2-yl)piperidine-4-carboxylate

Product 1

HCID 583031181-(5-Fluoropyridin-2-yl)piperidine-4-carboxylic acidYield 83%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5′-fluoro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester (12.5 g, 0.0495 mol) in THF (60 mL), H2O (60 mL) and MeOH (6 mL) was added LiOH.H2O (2.6 g, 0.0172 mol). 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 white precipitate was filtered off and dried to yield 9.2 g (83%) of 5′-fluoro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid. ES-MS m/e: 223.1 (M−H+)

Workup

  1. customwere removed under vacuo
  2. filtrationthe white precipitate was filtered off
  3. customdried

Sources & evidence

ORD record
ord-70614860799e4f5bb8a12cdc06ac78fd
Source dataset
uspto-grants-2013_08
Patent number
US08507535B2

Reaction notes

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