Potassium Permanganate → 7alpha-Carboxyandrostane-3,17-dione

HRID 42123Notes

Reaction equation

HRID 42123 reaction equation
[CH:1]([C@@H:3]1[CH2:20][CH:19]2[C@:14]([CH3:22])([CH2:15][CH2:16][C:17](=[O:21])[CH2:18]2)[C@@H:13]2[C@@H:4]1[C@H:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:23])[CH2:7][CH2:6]1)=[O:2].[O-:24][Mn](=O)(=O)=O.[K+]>>[C:1]([C@@H:3]1[CH2:20][CH:19]2[C@:14]([CH3:22])([CH2:15][CH2:16][C:17](=[O:21])[CH2:18]2)[C@@H:13]2[C@@H:4]1[C@H:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:23])[CH2:7][CH2:6]1)([OH:24])=[O:2]

Participants

3

Reactant 2

HCID 516875Potassium PermanganateHCID 866355927alpha-Formylandrostane-3,17-dione

Product 1

HCID 690102647alpha-Carboxyandrostane-3,17-dioneYield 96%

Procedure

To a stirred suspension of 7α-formylandrostane-3,17-dione (1.77 g) in t-ButOH (35 mL) and 5% aqueous Na2HPO4 solution (21.5 mL), 1N aqueous KMnO4 (35 mL) was added. After 5 minutes at room temperature, the mixture was quenched by addition of 40% aqueous NaHSO3 solution. The suspension was filtered, washed with H2O and the filtrate was freeze-dried. The residue was taken up with H2O (50 mL) and extracted with EtOAc (4×70 mL). The combined organic extracts were dried over Na2SO4 and evaporated to dryness to give 7α-carboxyandrostane-3,17-dione (1.80 g, 96%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 12.00 (1H, bb), 2.65 (1H, m), 2.45-0.70 (20H, m), 1.00 (3H, s), 0.79 (3H, s).

Workup

  1. additionwas added
  2. customthe mixture was quenched by addition of 40% aqueous NaHSO3 solution
  3. filtrationThe suspension was filtered
  4. washwashed with H2O
  5. customthe filtrate was freeze-dried
  6. extractionextracted with EtOAc (4×70 mL)
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-67c87e2f045d4064982b3f4805239293
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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