Water → HCID 70609230, compound

HRID 2163143Notes

Reaction equation

HRID 2163143 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][C@H:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C@H:8]([OH:18])[CH2:7]2)=O)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH:1]1([CH2:4][N:6]2[CH2:11][CH2:10][C@H:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C@H:8]([OH:18])[CH2:7]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 70609347HCID 70609347, compound

Product 1

HCID 70609230HCID 70609230, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

cis-1-Cyclopropylcarbonyl-4-phenyl-3-piperidinol (10.01 g, 41.1 mmoles, described above) is suspended in dry tetrahydrofuran (250 ml) and added dropwise to a suspension of lithium aluminum hydride (5.0 g, 94.7 mmoles) in tetrahydrofuran. The mixture is stirred at room temperature for 2 hours. Water (60 ml) is added slowly to the cooled reaction mixture, followed by aqueous sodium hydroxide (60 ml, 3N). The gelatinous precipitate is removed by filtration and the filtrate evaporated. The solid residue is dissolved in methylene chloride, washed with brine, dried (MgSO4) and evaporated. The residue is crystallized from hexane to give the title compound, mp 98°-100° C.

Workup

  1. customThe gelatinous precipitate is removed by filtration
  2. customthe filtrate evaporated
  3. dissolutionThe solid residue is dissolved in methylene chloride
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue is crystallized from hexane

Sources & evidence

ORD record
ord-1cbff2f258ca407b98e6ba08aae7babf
Source dataset
uspto-grants-1979_01
Patent number
US04132710

Reaction notes

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