Lithium Hydroxide → 3-[1-(4-Tert-butyl-phenyl)-piperidin-4-yl]-propionic acid lithium salt

HRID 511184Notes

Reaction equation

HRID 511184 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.[OH-].[Li+:24].O1CCCC1>O.C(#N)C>[Li+:24].[C:18]([C:15]1[CH:14]=[CH:13][C:12]([N:9]2[CH2:10][CH2:11][CH:6]([CH2:5][CH2:4][C:3]([O-:22])=[O:2])[CH2:7][CH2:8]2)=[CH:17][CH:16]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 585763793-[1-(4-Tert-butyl-phenyl)-piperidin-4-yl]-propionic acid methyl ester

Product 1

HCID 585759763-[1-(4-Tert-butyl-phenyl)-piperidin-4-yl]-propionic acid lithium salt

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 3-[1-(4-tert-butyl-phenyl)-piperidin-4-yl]-propionic acid methyl ester (295 mg; 0.97 mmol, prepared in accordance with Example 145) is added lithium hydroxide (72 mg; 3.00 mmol) dissolved in water (6.5 mL). After dilution with tetrahydrofuran (10 mL) the reaction mixture is stirred for 2-4 hours. The mixture is then diluted with acetonitrile until a precipitate is formed. The solid is collected by filtration and dried under high vacuum to deliver the desired product (468 mg) which is used in the next step without further purification.

Workup

  1. customis formed
  2. filtrationThe solid is collected by filtration
  3. customdried under high vacuum
  4. customis used in the next step without further purification

Sources & evidence

ORD record
ord-755d8b18423240c894b081756c8a8013
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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