Lithium Hydroxide → HCID 68687439, compound

HRID 2245353Notes

Reaction equation

HRID 2245353 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:11]([NH2:12])[CH2:10][CH2:9][N:8]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[CH2:7]1)=[O:5])C.[OH-].[Li+]>C1COCC1.CO.O>[NH2:12][C@H:11]1[CH2:10][CH2:9][N:8]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[CH2:7][C@@H:6]1[C:4]([OH:5])=[O:3]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 68685046HCID 68685046, compound

Product 1

HCID 68687439HCID 68687439, compoundYield 37.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(3R,4R) and (3S,4S)-4-Amino-1-[2-(3,4-dimethoxy-phenyl)-ethyl]-piperidine-3-carboxylic acid ethyl ester (262 mg) and lithium hydroxide (166 mg) in 5 ml THF, 5 ml MeOH and 1 ml H2O were stirred for 24 h at ambient temperature. The mixture was diluted with buffer pH 7 and extracted with AcOEt. The combined organic layers were washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure gave an oil which was purified by column chromatography (Isolute SPE Flash NH2, AcOEt) and precipitated (AcOEt/heptane) to give 90 mg (37%) of the title compound as a white solid.

Workup

  1. additionThe mixture was diluted with buffer pH 7
  2. extractionextracted with AcOEt
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent under reduced pressure
  6. customgave an oil which
  7. customwas purified by column chromatography (Isolute SPE Flash NH2, AcOEt)
  8. customprecipitated (AcOEt/heptane)

Sources & evidence

ORD record
ord-265f5af2f3d045878a3f2d94069dbff7
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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