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

HRID 511174Notes

Reaction equation

HRID 511174 reaction equation
C[O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1.[OH-].[Li+:25].O1CCCC1>O.C(#N)C>[Li+:25].[C:19]([C:16]1[CH:15]=[CH:14][C:13]([N:10]2[CH2:11][CH2:12][CH:7]([CH2:6][CH2:5][CH2:4][C:3]([O-:23])=[O:2])[CH2:8][CH2:9]2)=[CH:18][CH:17]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 585760674-[1-(4-Tert-butyl-phenyl)-piperidin-4-yl]-butyric acid methyl ester

Product 1

HCID 585766364-[1-(4-Tert-butyl-phenyl)-piperidin-4-yl]-butyric acid lithium saltYield 138.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 4-[1-(4-tert-butyl-phenyl)-piperidin-4-yl]-butyric acid methyl ester (385 mg; 1.21 mmol, prepared in accordance with Example 135) 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 afford the desired product (517 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

Sources & evidence

ORD record
ord-5002861191fb476999622f5c4dc2a043
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

Loading…