Butanal → HCID 10921267, compound

HRID 1870224Notes

Reaction equation

HRID 1870224 reaction equation
[OH:1][C@H:2]1[C@H:7]([CH2:8][OH:9])[CH2:6][CH2:5][NH:4][CH2:3]1.[CH:10](=O)[CH2:11][CH2:12][CH3:13].S1C=CC=C1>CO.[Pd]>[CH2:10]([N:4]1[CH2:5][CH2:6][C@@H:7]([CH2:8][OH:9])[C@H:2]([OH:1])[CH2:3]1)[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 261ButanalHCID 8030ThiopheneHCID 55287217HCID 55287217, compound

Product 1

HCID 10921267HCID 10921267, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate (1-a) (0.022 mol) and butanal (0.025 mol) in methanol (150 ml) was hydrogenated with palladium on activated carbon (10%) (1 g) as a catalyst in the presence of a solution of thiophene (4% in THF) (1 ml). After uptake of H2 (1 equiv.), the catalyst was filtered off and the filtrate was evaporated, yielding 4.1 g of (±)-trans-1-butyl-3-hydroxy-4-piperidinemethanol (interm. 1-b) (99.5%, used in next reaction step without further purification).

Workup

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

Sources & evidence

ORD record
ord-1fd6db96a32f4e5db3379a678ad98356
Source dataset
uspto-grants-2000_08
Patent number
US06096761

Reaction notes

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