Water → HCID 59900540, compound

HRID 2228769Notes

Reaction equation

HRID 2228769 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][C@@H:17]([CH3:20])[CH2:16][C@@H:15]1[C:21]([NH2:23])=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>O1CCCC1>[NH3:14].[CH2:7]([N:14]1[CH2:19][CH2:18][C@@H:17]([CH3:20])[CH2:16][C@@H:15]1[CH2:21][NH2:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 53986202HCID 53986202, compound

Product 2

HCID 222AmmoniaHCID 59900540HCID 59900540, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (9.2 ml, 1 M in tetrahydrofuran, 9.2 mmol) was added to a solution of (2R,4R)-1-benzyl-4-methyl-2-piperidinecarboxamide (preparation 86) (3.5 g, 15.0 mmol) in tetrahydrofuran (60 ml), and the reaction heated under reflux ovemight. The reaction was cooled in an ice-bath, water (0.4 ml), 15% NaOH solution (0.4 ml), and water (1.2 ml) were added consecutively, and the resulting precipitate filtered off. The filtrate was concentrated under reduced pressure, re-dissolved in dichloromethane and washed with brine, dried over Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (100:0:0 to 85:15:1) to give the title compound as a yellow oil, (650 mg, 20%).

Workup

  1. temperaturethe reaction heated
  2. temperatureunder reflux ovemight
  3. temperatureThe reaction was cooled in an ice-bath
  4. filtrationthe resulting precipitate filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutionre-dissolved in dichloromethane
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated under reduced pressure
  10. customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane

Sources & evidence

ORD record
ord-073a98b8362a4a3c973e629cf3e443f7
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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