Dihydrocholesterol → 3-Oxocholestane

HRID 842495

Reaction equation

HRID 842495 reaction equation
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:28])[CH2:14][CH2:15][C@@H:16]3[C@@:21]4([CH3:27])[CH2:22][CH2:23][C@H:24]([OH:26])[CH2:25][C@@H:20]4[CH2:19][CH2:18][C@H:17]3[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7]>C(OCC)C.[Os](=O)(=O)(=O)=O>[CH3:8][CH:6]([CH2:5][CH2:4][CH2:3][C@H:2]([C@@H:9]1[C@:13]2([CH3:28])[C@H:12]([C@H:17]3[C@H:16]([CH2:15][CH2:14]2)[C@:21]2([CH3:27])[CH:20]([CH2:25][C:24](=[O:26])[CH2:23][CH2:22]2)[CH2:19][CH2:18]3)[CH2:11][CH2:10]1)[CH3:1])[CH3:7]

Participants

4

Reactant 1

HCID 6665Dihydrocholesterol

Product 1

HCID 108835733-OxocholestaneYield 90%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

2.5 Millimole of 3β-cholestanol was dissolved in 50 ml of diethyl ether, and MCOsOx containing osmium tetroxide in an amount equivalent to 2.5 mmol was added thereto, followed by stirring at 25° C. for 30 hours to cause a reaction to take place. MCOsOx was removed from the reaction solution, and a crude keto compound was recovered from the filtrate and purified by silica gel column chromatography (eluent:benzene) to give 3-cholestanon at a yield of 90%.

Workup

  1. additionwas added
  2. customa reaction
  3. customMCOsOx was removed from the reaction solution
  4. customa crude keto compound was recovered from the filtrate
  5. custompurified by silica gel column chromatography (eluent:benzene)

Sources & evidence

ORD record
ord-494ce304ac974530a2dfaf1a4fa9e2dd
Source dataset
uspto-grants-2002_04
Patent number
US06376419B1

Linked notes

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