Water → (2S,3R,4S)-2,3,4-Trihydroxycyclohexanone

HRID 389374Notes

Reaction equation

HRID 389374 reaction equation
[OH:1][C@@H:2]1[C@@H:7]([OH:8])[C@H:6]([OH:9])[C:5](=[O:10])[CH:4]=[CH:3]1.O>CO.[Pd]>[OH:8][C@H:7]1[C@H:6]([OH:9])[C@@H:5]([OH:10])[CH2:4][CH2:3][C:2]1=[O:1]

Participants

5

Reactant 2

HCID 962WaterHCID 44511908HCID 44511908, compound

Product 1

HCID 45082801(2S,3R,4S)-2,3,4-TrihydroxycyclohexanoneYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

205 mg of (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one obtained in Example 3 was dissolved in 3.5 mL of methanol. 20 mg (50 weight % of water contained) of 5 weight % Pd/C was added thereto and hydrogenated at room temperature (25 degrees centigrade) under ordinary pressure (1 atm). After the completion of the reaction, the catalyst was removed by filtration, and the filtrate was concentrated to obtain 198 mg (yield: 96%) of (2S,3R,4S)-2,3,4-trihydroxycyclohexane-1-one.

Workup

  1. customhydrogenated at room temperature
  2. custom(25 degrees centigrade)
  3. customAfter the completion of the reaction
  4. customthe catalyst was removed by filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c25bac5a1b794539b0ff197a9ac631f9
Source dataset
uspto-grants-2013_02
Patent number
US08378146B2

Reaction notes

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