Water → 3alpha,20-Dihydroxy-20-methyl-5alpha-pregnane

HRID 232813Notes

Reaction equation

HRID 232813 reaction equation
C([O:4][C@@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=O)C.[CH3:27][Mg]Br.[Cl-].[NH4+].O>C1C=CC=CC=1>[OH:4][C@@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15]([OH:17])([CH3:16])[CH3:27])[CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 53835422Allopregnan-3alpha-ol-20-one acetateHCID 178418573HCID 178418573, compound3×

Product 1

HCID 677076803alpha,20-Dihydroxy-20-methyl-5alpha-pregnane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred mixture of 3α-acetoxy-5α-pregnan-20-one (120 mg, 360.5 g/m, 0.32 mmol) in 25 mL of dry benzene, was added 4.6 mL of 3M methylmagnesium bromide dropwise. After the addition of methylmagnesium bromide was completed, the reaction mixture was allowed to stir at room temperature for 18 h and then refluxed for 2 h. The excess methylmagnesium bromide was decomposed by dropwise addition of 30 mL of saturated ammonium chloride solution in an ice bath. The solution product was poured into water and extracted with chloroform twice. The extracts were dried over magnesium sulfate and evaporated to give 110 mg of crude product. The product was recrystallized in methanol to give 83 mg of 3α,20-dihydroxy-20-methyl-5α-pregnane.

Workup

  1. temperaturerefluxed for 2 h
  2. extractionextracted with chloroform twice
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. customevaporated
  5. customto give 110 mg of crude product
  6. customThe product was recrystallized in methanol

Sources & evidence

ORD record
ord-eb7770b6fc884ee1aecaf802c10efb8f
Source dataset
uspto-grants-1997_01
Patent number
US05591733

Reaction notes

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