Lithium hydroxide, monohydrate → HCID 58302997, compound

HRID 1891329Notes

Reaction equation

HRID 1891329 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:13]=[N:14][C:15]([C:18]#[N:19])=[CH:16][CH:17]=2)[CH2:8][CH2:7]1)=[O:5])C.O[Li].O>C1COCC1.O.CO>[C:18]([C:15]1[N:14]=[CH: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)#[N:19]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58302996HCID 58302996, compound

Product 1

HCID 58302997HCID 58302997, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6′-cyano-3,4,5,6-tetrahydro-2H-[1,3]bipyridinyl-4-carboxylic acid ethyl ester (1.61 g, 6.20 mmol) in THF (30 mL), H2O (30 mL) and MeOH (3 mL) was added LiOH.H2O (326 mg, 7.76 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 1.40 g (99%) of 6′-cyano-3,4,5,6-tetrahydro-2H-[1,3]bipyridinyl-4-carboxylic acid. ES-MS m/e: 230.1 (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-ff890e8ffe0446fd99b3a325b011e18e
Source dataset
uspto-grants-2013_08
Patent number
US08507535B2

Reaction notes

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