Lithium Hydroxide → HCID 15295465, compound

HRID 2210548Notes

Reaction equation

HRID 2210548 reaction equation
C([O:3][C:4](=[O:27])[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:14]=2)[CH2:9][CH2:8]1)=[O:6])C.[OH-].[Li+]>C1COCC1.O>[CH:22]1([O:21][C:15]2[CH:14]=[C:13]([CH:10]3[CH2:9][CH2:8][N:7]([C:5](=[O:6])[C:4]([OH:27])=[O:3])[CH2:12][CH2:11]3)[CH:18]=[CH:17][C:16]=2[O:19][CH3:20])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 15295464HCID 15295464, compound

Product 1

HCID 15295465HCID 15295465, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-[4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]-2-oxo-acetic acid ethyl ester (14.1 mmol, 5.3 g) in THF (140 mL) was added aqueous lithium hydroxide solution (1.0M; 17.6 mmol, 17.6 mL) in one portion at room temperature and the resulting homogeneous solution stirred overnight. The precipitated solution was diluted with H2O (150 mL) and the THF was removed in vacuo. The aqueous phase was diluted with saturated NaHCO3 (400 mL), and acidified with 2N HCl. The aqueous phase was then extracted with EtOAc (3×400 mL) and the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The product was triturated with Et2O/hexane to yield the title compound as a white solid, mp=112°-113° C. (10.8 mmol, 3.74 g, 76%).

Workup

  1. customthe THF was removed in vacuo
  2. additionThe aqueous phase was diluted with saturated NaHCO3 (400 mL)
  3. extractionThe aqueous phase was then extracted with EtOAc (3×400 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe product was triturated with Et2O/hexane

Sources & evidence

ORD record
ord-b3deedc4af854fadaac6c120d253bfc8
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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