Lithium Hydroxide → HCID 68686898, compound

HRID 2245355Notes

Reaction equation

HRID 2245355 reaction equation
C([O:3][C:4]([CH:6]1[CH:11]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:9][N:8]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].[OH-].[Li+]>C1COCC1.O>[C:16]([O:15][C:13]([NH:12][CH:11]1[CH2:10][CH2:9][N:8]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[CH2:7][CH:6]1[C:4]([OH:5])=[O:3])=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 68685280HCID 68685280, compound

Product 1

HCID 68686898HCID 68686898, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of rac-4-tert-butoxycarbonylamino-1-(3,4-dimethoxy-phenyl)-piperidine-3-carboxylic acid ethyl ester (170 mg) in 2 ml THF, were added 1 ml NaOH 1M and lithium hydroxide (100 mg). The suspension was stirred 22 h at RT., diluted with water and extracted twice with tert-butylmethylether. The aqueous layer was acidified to pH 4, saturated with NaCl and then the product was extracted with 3 portions of AcOEt. The organic layers were dried over MgSO4, filtered, evaporated and chromatographed (silica gel, AcOEt) to provide the title compound (38 mg, 55%).

Workup

  1. extractionextracted twice with tert-butylmethylether
  2. extractionthe product was extracted with 3 portions of AcOEt
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customchromatographed (silica gel, AcOEt)

Sources & evidence

ORD record
ord-ee515ad4f80648b08e9c3d2410560007
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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