HCID 69997935, compound → HCID 56994186, compound

HRID 566891Notes

Reaction equation

HRID 566891 reaction equation
[C:1]([O:9][C@H:10]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@@H:12]([CH2:13][CH2:14][C:15]3[C:16]4[C@:24]([CH3:32])([CH2:25][CH2:26][C:27]=32)[C@@H:19]([C@H:20]([CH3:23])[CH2:21][OH:22])[CH2:18][CH:17]=4)[C:11]1([CH3:34])[CH3:33])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[C:1]([O:9][C@H:10]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@@H:12]([CH2:13][CH2:14][C:15]3[C:16]4[C@:24]([CH3:32])([CH2:25][CH2:26][C:27]=32)[C@@H:19]([C@@H:20]([CH:21]=[O:22])[CH3:23])[CH2:18][CH:17]=4)[C:11]1([CH3:33])[CH3:34])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69997935HCID 69997935, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 56994186HCID 56994186, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

—Pyridinium chlorochromate (8.79 g) was added to a solution of (3β,5α,20S)-4,4,20-trimethylpregna-8,14-diene-3,21-diol 3-benzoate (Example 7, step ii; 12.6 g) in dry dichloromethane (130 ml). The reaction mixture was stirred at room temperature for 1.5 h. Another portion of pyridinium chlorochromate (1.50 g) was added and stirring was continued for another 1.5 h. The reaction mixture was filtered and the filtrate was poured into a saturated aqueous solution of sodium hydrogencarbonate. The product was extracted into dichloromethane and the combined organic phases were washed with water, dried over magnesium sulfate and concentrated under reduced pressure, to afford (3β,5α,20S)-3-(benzoyloxy)-4,4-dimethylpregna-8,14-diene-20-carboxaldehyde (10.3 g). The product was used in the following step without further purification.

Workup

  1. stirringstirring
  2. waitwas continued for another 1.5 h
  3. filtrationThe reaction mixture was filtered
  4. additionthe filtrate was poured into a saturated aqueous solution of sodium hydrogencarbonate
  5. extractionThe product was extracted into dichloromethane
  6. washthe combined organic phases were washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9b6f1333d5f843a2b541071c36d74f58
Source dataset
uspto-grants-2001_01
Patent number
US06177420B1

Reaction notes

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