Water → HCID 59900540, compound

HRID 567841Notes

Reaction equation

HRID 567841 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 aluminum hydride (9.2 ml, 1M 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 overnight. 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 overnight
  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-ffa0ceccd83042b6a79e72eb5b6e5d80
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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