Water → HCID 25134321, compound

HRID 1970929Notes

Reaction equation

HRID 1970929 reaction equation
[CH3:1][CH2:2][C@@H:3]([CH:28]([CH3:30])[CH3:29])/[CH:4]=[CH:5]/[C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:27])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7].CS(N)(=O)=[O:33].[K].C(=O)([O-])[O-].[K+].[K+].S(=O)(=O)(O)[O-].[Na+].[OH2:49]>C(O)(C)(C)C>[OH:49][C@@H:5]([C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:27])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7])[C@@H:4]([OH:33])[C@H:3]([CH:28]([CH3:29])[CH3:30])[CH2:2][CH3:1]

Participants

8

Reactant 6

HCID 962WaterHCID 11430Potassium CarbonateHCID 72879MethanesulfonamideHCID 516919Sodium BisulfateHCID 5462222PotassiumHCID 6442194Stigmastadienone

Product 1

HCID 25134321HCID 25134321, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

420 mg of (22E)-stigmasta-4,22-dien-3-one are dissolved in 100 mL of tert-butanol and the same volume of water is added. To this mixture 0.93 g of the chiral auxiliary DHQD2-Phal, 450 mg (2 mmol) methanesulphonamide, 4.5 g of potassium ferricianide, 2 g of potassium carbonate and 30 mg de potassium osmate are added. The mixture is vigorously stirred, at ambient temperature, during 9 days. The reaction, controlled by thin layer chromatography is not completed. Little portions of solid sodium bisulphate are added, until bubbling stops. The mixture is extracted with ethyl acetate, washed with 0.25M aqueous sulphuric acid, then with 10% NaOH 10%, and finally with water. The organic phase is dried and evaporated. The crude product is purified by column chromatography (eluting solvent: hexane/ethyl acetate 1:1). 180 mg of (22S,23S)-22,23-dihydroxystigmast-4-en-3-one are obtained, subsequently 165 mg of (22R,23R)-22,23-dihydroxystigmast-4-en-3-one are eluted.

Workup

  1. customThe reaction
  2. customuntil bubbling stops
  3. extractionThe mixture is extracted with ethyl acetate
  4. washwashed with 0.25M aqueous sulphuric acid
  5. customThe organic phase is dried
  6. customevaporated
  7. customThe crude product is purified by column chromatography (eluting solvent: hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-c47722fc09cf409ba0c698eea4bb6a81
Source dataset
uspto-grants-2013_04
Patent number
US08431554B2

Reaction notes

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