Barium thiocyanate → 3alpha-Hydroxy-21-thiocyanato-5alpha-pregnane-11,20-dione

HRID 1077010Notes

Reaction equation

HRID 1077010 reaction equation
Br[CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C@H:13]([OH:24])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[S-:26][C:27]#[N:28].[Ba+2].[S-]C#N>CC(C)=O.O>[OH:24][C@@H:13]1[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[C:19](=[O:23])[CH2:20][C@@:21]2([CH3:22])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:3](=[O:25])[CH2:2][S:26][C:27]#[N:28])[CH2:12]1

Participants

5

Reactant 2

HCID 164928Barium thiocyanateHCID 8673346721-Bromo-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Product 1

HCID 867334693alpha-Hydroxy-21-thiocyanato-5alpha-pregnane-11,20-dioneYield 96.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 21-bromo-3α-hydroxy-5α-pregnane-11,20-dione (0.75 g.) in acetone (50 ml.) was treated with a solution of barium thiocyanate (2.6 g.) in water (10 ml.). The resulting mixture was refluxed for 4 hr., cooled and then partitioned between water and ether. The organic layer was washed with water, dried (Na2SO4) and evaporated. The residue (720 mg.) was purified by preparative t.l.c. (EtOAc) to afford title compound (685 mg.) as a white foam, [α]D + 67°.

Workup

  1. temperatureThe resulting mixture was refluxed for 4 hr
  2. temperature, cooled
  3. custompartitioned between water and ether
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue (720 mg.) was purified by preparative t.l.c

Sources & evidence

ORD record
ord-f95ae8a8889449b3b1f6a56d6a96519a
Source dataset
uspto-grants-1976_05
Patent number
US03959260

Reaction notes

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