HCID 67602990, compound → HCID 67602217, compound

HRID 362782Notes

Reaction equation

HRID 362782 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:8]([OH:9])[CH2:7][CH2:6][N:5](CC2C=CC=CC=2)[CH2:4]1.[H][H]>[Pd].CO>[CH3:1][O:2][C@H:3]1[C@@H:8]([OH:9])[CH2:7][CH2:6][NH:5][CH2:4]1

Participants

5

Reactant 2

HCID 67602990HCID 67602990, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67602217HCID 67602217, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 11.5 g of intermediate (2) and 150 ml of methanol was hydrogenated at normal pressure and at room temperature with 2 g of palladium-on-charcoal catalyst (10%). After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel (eluent: CHCl3 /(CH3OH/NH3) 85/15). The pure fractions were collected and the eluent was evaporated, yielding 3.6 g (53%) of cis-3-methoxy-4-piperidinol as an oily residue (intermediate 3).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column-chromatography over silica gel (eluent: CHCl3 /(CH3OH/NH3) 85/15)
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated

Sources & evidence

ORD record
ord-486c7de7621d4461bde21fae00347569
Source dataset
uspto-grants-1999_02
Patent number
US05872131

Reaction notes

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