Potassium Permanganate → HCID 69014555, compound

HRID 42089Notes

Reaction equation

HRID 42089 reaction equation
[CH:1]([C@@H:3]1[CH:20]2[C@:15]([CH3:22])([CH2:16][CH2:17][C:18](=[O:21])[CH2:19]2)[C@@H:14]2[C@H:5]([C@H:6]3[C@@:10]([CH2:12][CH2:13]2)([CH3:11])[C:9](=[O:23])[CH2:8][CH2:7]3)[CH2:4]1)=[O:2].[O-:24][Mn](=O)(=O)=O.[K+]>>[C:1]([C@@H:3]1[CH:20]2[C@:15]([CH3:22])([CH2:16][CH2:17][C:18](=[O:21])[CH2:19]2)[C@@H:14]2[C@H:5]([C@H:6]3[C@@:10]([CH2:12][CH2:13]2)([CH3:11])[C:9](=[O:23])[CH2:8][CH2:7]3)[CH2:4]1)([OH:24])=[O:2]

Participants

3

Reactant 2

HCID 516875Potassium PermanganateHCID 866355666alpha-Formylandrostane-3,17-dione

Product 1

HCID 69014555HCID 69014555, compoundYield 96%

Procedure

To a stirred suspension of 6α-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 6α-carboxyandrostane-3,17-dione (1.80 g, 96%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 11.99 (1H, bb), 2.46-0.73 (21H, m), 1.01 (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-cfd7f0567da74d15b72aa5d292838452
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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