Calciumoxide → HCID 11447366, compound

HRID 1870225Notes

Reaction equation

HRID 1870225 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C@H:11]([CH2:14][OH:15])[C@H:10]([OH:16])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-2].[Ca+2]>O1CCCC1.[Cr]([O-])([O-])=O.[Cu+2]>[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C@H:11]([CH2:14][OH:15])[C@H:10]([OH:16])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C@@H:11]([CH2:14][OH:15])[C@H:10]([OH:16])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 6850728CalciumoxideHCID 58635328HCID 58635328, compound

Product 2

HCID 11447366HCID 11447366, compoundHCID 58635328HCID 58635328, compound

Reagents, catalysts & solvents 2

HCID 178505374HCID 178505374, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (±)-cis-1-(phenylmethyl)-3-hydroxy-4-piperidinemethanol (0.11 mol) and calcium oxide (5 g) in tetrahydrofuran (250 ml) was hydrogenated with copper chromite (CuO.Cr2O3) (4 g) as a catalyst at 120° C. The catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography (CH2Cl2 /CH3OH/CH3OH(NH3): 93/5/2). The fractions were evaporated, yielding 8.5 g of (±)-cis-1-(phenylmethyl)-3-hydroxy-4-piperidinemethanol and 6.32 g of (±)-trans-1-(phenylmethyl)-3-hydroxy-4-piperidinemethanol.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography (CH2Cl2 /CH3OH/CH3OH(NH3): 93/5/2)
  4. customThe fractions were evaporated

Sources & evidence

ORD record
ord-27a3d758d3b9475eb1d01f66232bb172
Source dataset
uspto-grants-2000_08
Patent number
US06096761

Reaction notes

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