Hydrochloric Acid → Allopregnanediol

HRID 2253814Notes

Reaction equation

HRID 2253814 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][CH:13]=[C:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=O)C.[Na].Cl>C(O)(C)C>[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@@H:15]([OH:17])[CH3:16])[CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1738151HCID 1738151, compoundHCID 5360545Sodium2×

Product 1

HCID 164674AllopregnanediolYield 9.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of 3α-acetoxy-5α-pregn-16-en 20-one (970 mg, 358.5 g/m, 2.7 mmol) in 130 mL of dry isopropanol was added sodium metal (8.0 g, 23 g/m, 348 mmol) slowly in small portions over 1 hr. After refluxing for 1 hour and additional amount of sodium (3.5 g) was added and reflux continued for 1 hour. The reaction mixture was acidified with 10% HCl and extracted with chloroform. The organic phase was dried over magnesium sulfate and concentrated to give the crude product. Recrystallization from acetone with cooling in the freezer gave 80 mg of a mixture (93:7) of 20α and 20β respectively. Additional recrystallization from methanol resulted in the pure titled product.

Workup

  1. temperatureAfter refluxing for 1 hour
  2. temperaturereflux
  3. extractionextracted with chloroform
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give the crude product
  7. customRecrystallization from acetone
  8. temperaturewith cooling in the freezer

Sources & evidence

ORD record
ord-4dc512ee22d24ef9aa49303530168910
Source dataset
uspto-grants-1993_08
Patent number
US05232917

Reaction notes

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