Lithium Hydroxide → HCID 22467912, compound

HRID 1935211Notes

Reaction equation

HRID 1935211 reaction equation
C[O:2][C:3](=[O:23])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)[C:3]([OH:23])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67483374HCID 67483374, compound

Product 1

HCID 22467912HCID 22467912, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-pyridin-4-yl-phenyl)-propionic acid methyl ester (240 mg, 0.78 mmol) in tetrahydrofuran (3 mL) was treated with a 0.8M aqueous lithium hydroxide solution (1.45 mL, 1.16 mmol). The resulting reaction mixture was stirred at 25° C. for 30 min and then heated under reflux for 15 h. The reaction mixture was allowed to cool to 25° C. and then partitioned between water (100 mL) and ethyl acetate (70 mL). The layers were separated, and the aqueous layer was further extracted with ethyl acetate (1×30 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford a yellow oil that solidified upon sitting. The solid was collected to afford 3-cyclopentyl-2-(4-pyridin-4-yl-phenyl)-propionic acid (127 mg, 55%) as a yellow solid: mp 118-121° C.; FAB-HRMS m/e calcd for C19H21NO2 (M+H)+ 296.1650, found 296.1658.

Workup

  1. customThe resulting reaction mixture
  2. temperatureheated
  3. temperatureunder reflux for 15 h
  4. temperatureto cool to 25° C.
  5. custompartitioned between water (100 mL) and ethyl acetate (70 mL)
  6. customThe layers were separated
  7. extractionthe aqueous layer was further extracted with ethyl acetate (1×30 mL)
  8. dry with materialThe combined organic extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto afford a yellow oil
  12. customThe solid was collected

Sources & evidence

ORD record
ord-41ae5486a9194498b937b76fc15fc5b2
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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