Lithium Hydroxide → HCID 59149677, compound

HRID 2069314Notes

Reaction equation

HRID 2069314 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1)=[O:5])C.[OH-].[Li+]>CO.O1CCOCC1.O>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:11]=[CH:10][C:9]([C@@H:7]3[CH2:8][C@H:6]3[C:4]([OH:5])=[O:3])=[CH:14][CH:13]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 59149664HCID 59149664, compound

Product 1

HCID 59149677HCID 59149677, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

3.00 g (10.5 mmol) of trans-2-[6-(4-fluoro-phenyl)-pyridin-3-yl]-cyclopropanecarboxylic acid ethyl ester and 378 mg (15.8 mmol) of lithium hydroxide were dissolved in a mixture of 27 ml of methanol, 5 ml of dioxane and 3 ml of water, and the mixture was heated at 70° C. for 2 h. Subsequently, the mixture was evaporated to dryness, the residue was taken up in water and the pH was adjusted to 4 with acetic acid. The precipitate was isolated by filtration and purified by column chromatography (silica gel, dichloromethane/methanol, gradient from 98:2 to 95:5). Yield: 2.2 g.

Workup

  1. customSubsequently, the mixture was evaporated to dryness
  2. customThe precipitate was isolated by filtration
  3. custompurified by column chromatography (silica gel, dichloromethane/methanol, gradient from 98:2 to 95:5)

Sources & evidence

ORD record
ord-e274185a5ace47a79b0bc7f2bbf07d61
Source dataset
uspto-grants-2012_10
Patent number
US08299102B2

Reaction notes

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