Ethanol → HCID 86620232, compound

HRID 2040946Notes

Reaction equation

HRID 2040946 reaction equation
[CH3:1][C:2](=O)[C@@H:3]1[C@:20]2([CH3:21])[C@H:6]([C@H:7]3[C@H:17]([CH2:18][CH2:19]2)[C@:15]2([CH3:16])[C@H:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:9][CH2:8]3)[CH2:5][CH2:4]1.C(O)C.[NH2:26][OH:27].C([O-])(=O)C.[Na+]>ClCCl.O>[CH3:1][C:2](=[N:26][OH:27])[C@@H:3]1[C@:20]2([CH3:21])[C@H:6]([C@H:7]3[C@H:17]([CH2:18][CH2:19]2)[C@:15]2([CH3:16])[C@H:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:9][CH2:8]3)[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 702Ethanol2×HCID 787HydroxylamineHCID 517045Sodium AcetateHCID 118088365alpha-Pregnan-20-one

Product 1

HCID 86620232HCID 86620232, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3α-fluor, 5α-pregnan-20-one (10 mmol) is dissolved in dichloromethane 5 mL and ethanol 50 mL at rt and air atmosphere, in a 250 mL round bottom flask. 4 equiv. of NH2OH chlorhydrate and 4 equiv. of sodium acetate are dissolved in 5 mL H2O and then added to the steroid solution. 20 mL of ethanol are added and the mixture put on reflux overnight. The mixture is then cooled and the solvent removed under reduced pressure. The white residue is then treated with 50 mL H2O and 50 mL dichloromethane, the aqueous phase extracted with 3×30 mL dichloromethane. The collected organic phases are then dried over MgSO4, filtrated and the solvent removed under reduced pressure. The final residue is purified by silica flash column chromatography (dichloromethane:diethyl ether 4:1). Quantitative yield.

Workup

  1. customat rt
  2. temperatureon reflux overnight
  3. temperatureThe mixture is then cooled
  4. customthe solvent removed under reduced pressure
  5. additionThe white residue is then treated with 50 mL H2O and 50 mL dichloromethane
  6. extractionthe aqueous phase extracted with 3×30 mL dichloromethane
  7. dry with materialThe collected organic phases are then dried over MgSO4
  8. filtrationfiltrated
  9. customthe solvent removed under reduced pressure
  10. customThe final residue is purified by silica flash column chromatography (dichloromethane:diethyl ether 4:1)

Sources & evidence

ORD record
ord-2398d0b63a94443db36d775759bb38d7
Source dataset
uspto-grants-2013_11
Patent number
US08580983B2

Reaction notes

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