Sulfuric Acid → HCID 86586581, compound

HRID 895853Notes

Reaction equation

HRID 895853 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[OH:11][C@H:12]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[CH:14]([CH2:15][CH2:16][C:17]3[C:18]4[C@:27]([CH3:35])([CH2:28][CH2:29][C:30]=32)[C@@H:21]([C@@H:22]([CH3:26])[CH2:23][C:24]#N)[CH2:20][CH:19]=4)[C:13]1([CH3:37])[CH3:36].S(=O)(=O)(O)[OH:39]>C1(C)C=CC=CC=1>[OH:11][C@H:12]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[CH:14]([CH2:15][CH2:16][C:17]3[C:18]4[C@:27]([CH3:35])([CH2:28][CH2:29][C:30]=32)[C@@H:21]([C@@H:22]([CH3:26])[CH2:23][CH:24]=[O:39])[CH2:20][CH:19]=4)[C:13]1([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21225700DiisobutylaluminumhydrideHCID 69790431HCID 69790431, compound

Product 1

HCID 86586581HCID 86586581, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

16 ml diisobutylaluminiumhydride (20% in toluene) were added dropwise to a solution of 920 mg (20S)-3β-hydroxy-4,4,20-trimethyl-pregna-8,14-dien-21-carbonitril in 60 ml toluene at a temperature of −72° C. The mixture was stirred for 2 h at the same temperature, poured into 2N sulfuric acid, extracted with ethyl acetate, washed with 2N sulfuric acid and then washed with a half saturated solution of sodium chloride. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 750 mg (20S)-3β-hydroxy-4,4,20-trimethyl-pregna-8,14-dien-21-carbaldehyde as a white solid, which was used without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with 2N sulfuric acid
  3. washwashed with a half saturated solution of sodium chloride
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b65320637ca4ed9b8f9b821be4ba24d
Source dataset
uspto-grants-2005_07
Patent number
US06916921B2

Reaction notes

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