Hydrochloric Acid → Pregnane-3alpha,20alpha-diol

HRID 232801Notes

Reaction equation

HRID 232801 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])[CH: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 120059Pregnane-3alpha,20alpha-diolYield 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 an 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 title product.

Workup

  1. additionwas added
  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-98ac38e38a9c491298ed6316a0332d98
Source dataset
uspto-grants-1997_01
Patent number
US05591733

Reaction notes

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