Sodium borohydride → Prostaglandin F3α

HRID 1076078Notes

Reaction equation

HRID 1076078 reaction equation
[BH4-].[Na+].[CH3:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][C@H:8]([OH:27])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:16]([CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:14](=[O:15])[CH2:13][C@H:12]1[OH:26]>CO>[CH3:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][C@H:8]([OH:27])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:16]([CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C@@H:14]([OH:15])[CH2:13][C@H:12]1[OH:26]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 5280937Prostaglandin E3

Product 1

HCID 5280940Prostaglandin F3α

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of sodium borohydride (70 mg.) in 5 ml. of ice-cold methanol is added dropwise with stirring to a solution of racemic PGE3 (22 mg.) in 1.5 ml. of methanol at 0° C. This mixture is stirred at 0° C. for 30 minutes, and is then stirred and allowed to warm to 25° C. during one hour. After evaporation, water (10 ml.) is added, and the mixture is acidified with one normal hydrochloric acid, saturated with sodium chloride, and extracted repeatedly with ethyl acetate. The combined extracts are washed with saturated aqueous sodium chloride solution, dried, and evaporated. The residue is chromatographed on 3 g. of acid-washed silica gel (Silicar CC4), eluting with 50 ml. of ethyl acetate and then with 50 ml. of 1% methanol in ethyl acetate, collecting 10 ml. fractions. The faster moving fractions are combined and evaporated to give racemic PGF3α ; same mobility as optically active PGF3α on TLC silica gel and silver-nitrate impregnated silica gel plates with the A IX system twice; mass spectrum spectral peaks same as for optically active PGF3α. The slower moving fractions are combined and evaporated to give racemic PGF3β ; m.p. 85°-92° C.; same mobility as optically active PGF3β on TLC silica gel plates as for PGF3β ; mass spectrum spectral peaks same as for optically active PGF3β.

Workup

  1. additionof ice-cold methanol is added dropwise
  2. customat 0° C
  3. stirringis then stirred
  4. temperatureto warm to 25° C. during one hour
  5. customAfter evaporation, water (10 ml.)
  6. additionis added
  7. extractionextracted repeatedly with ethyl acetate
  8. washThe combined extracts are washed with saturated aqueous sodium chloride solution
  9. customdried
  10. customevaporated
  11. customThe residue is chromatographed on 3 g
  12. washof acid-washed silica gel (Silicar CC4), eluting with 50 ml
  13. customof 1% methanol in ethyl acetate, collecting 10 ml
  14. customevaporated

Sources & evidence

ORD record
ord-105e614a29f54efbb61220d29832ed1f
Source dataset
uspto-grants-1976_05
Patent number
US03954851

Reaction notes

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