Acetic Acid → 20,20-Ethylenedioxy-16alpha-methyl-5alpha-pregnane-3alpha,11beta-diol

HRID 1701443Notes

Reaction equation

HRID 1701443 reaction equation
[BH4-].[Na+].[CH2:3]1[CH2:30][O:29][C:5]([C@@H:7]2[C@:24]3([CH3:25])[C@H:10]([C@H:11]4[C@H:21]([C:22](=[O:26])[CH2:23]3)[C@:19]3([CH3:20])[C@H:14]([CH2:15][C@H:16]([OH:27])[CH2:17][CH2:18]3)[CH2:13][CH2:12]4)[CH2:9][C@H:8]2[CH3:28])([CH3:6])[O:4]1.C(O)(=O)C>O.C(O)C.N1C=CC=CC=1>[CH2:30]1[CH2:3][O:4][C:5]([C@@H:7]2[C@:24]3([CH3:25])[C@H:10]([C@H:11]4[C@H:21]([C@@H:22]([OH:26])[CH2:23]3)[C@:19]3([CH3:20])[C@H:14]([CH2:15][C@H:16]([OH:27])[CH2:17][CH2:18]3)[CH2:13][CH2:12]4)[CH2:9][C@H:8]2[CH3:28])([CH3:6])[O:29]1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 7058361120,20-Ethylenedioxy-3alpha-hydroxy-16alpha-methyl-5alpha-pregnan-11-one

Product 1

HCID 7058614320,20-Ethylenedioxy-16alpha-methyl-5alpha-pregnane-3alpha,11beta-diolYield 43.4%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium borohydride (4.12 g) in water (41 ml) was added to a refluxing solution of 20,20-ethylenedioxy-3α-hydroxy-16α-methyl-5α-pregnan-11-one (7.55 g) in ethanol (375 ml) containing pyridine (7 drops). The mixture was refluxed for 1 hr. then cooled and glacial acetic acid added until no further effervescence occurred. The mixture was partitioned between 3%-aqueous sodium hydrogen carbonate and ethyl acetate. The aqueous portion was extracted with additional ethyl acetate. The combined organic extracts were washed with saturated brine solution, dried and evaporated to a white foam which crystallised from acetone-water to afford the title compound as white prisms (3.29 g),

Workup

  1. temperatureThe mixture was refluxed for 1 hr
  2. temperaturethen cooled
  3. customThe mixture was partitioned between 3%-aqueous sodium hydrogen carbonate and ethyl acetate
  4. extractionThe aqueous portion was extracted with additional ethyl acetate
  5. washThe combined organic extracts were washed with saturated brine solution
  6. customdried
  7. customevaporated to a white foam which
  8. customcrystallised from acetone-water

Sources & evidence

ORD record
ord-904b4863fe0a4124a3ffba8d17da812b
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

Loading…