HCID 11447366, compound → HCID 55287217, compound

HRID 1870223Notes

Reaction equation

HRID 1870223 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][C@@H:11]([CH2:14][OH:15])[C@H:10]([OH:16])[CH2:9]2)C=CC=CC=1>CO.[Pd]>[OH:16][C@H:10]1[C@H:11]([CH2:14][OH:15])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 1

HCID 11447366HCID 11447366, compound

Product 1

HCID 55287217HCID 55287217, compoundYield 107.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (±)-trans-1-(phenylmethyl)-3-hydroxy-4-piperidinemethanol (17.8 g, 0.085 mol) (already described in J. Med. Chem., 1973, 156) in methanol (250 ml) was hydrogenated, at 50° C., with palladium on activated carbon (10%) (2 g) as a catalyst. After uptake of H2 (1 equiv.), the catalyst was filtered off and the filtrate was evaporated, yielding 12 g of (±)-trans-3-hydroxy-4-piperidinemethanol (interm. 1-a) (quantitative yield; used in next reaction step, without further purification). The corresponding cis-isomer is known from J. Org. Chem., 1969, 34 (11).

Workup

  1. filtrationAfter uptake of H2 (1 equiv.), the catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-379447c91e1c4ca28656ee258aee046f
Source dataset
uspto-grants-2000_08
Patent number
US06096761

Reaction notes

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