Sodium borohydride → HCID 70477050, compound

HRID 464152Notes

Reaction equation

HRID 464152 reaction equation
[CH2:1]=[C:2]1[CH2:19][CH2:18][C@@:17]2([CH2:20][OH:21])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:22])=[CH:3]1.[BH4-].[Na+]>CO.O>[CH2:1]=[C:2]1[CH2:19][CH2:18][C@@:17]2([CH2:20][OH:21])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[OH:22])=[CH:3]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18599507HCID 18599507, compound

Product 1

HCID 70477050HCID 70477050, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-methylene-androst-4-ene-19-ol-17-one in methanol was added a 2 molar excess of sodium borohydride. The mixture was stirred overnight at room temperature, diluted with water, extracted with ethyl acetate, washed with water, the organic layer separated, and dried over anhydrous sodium sulfate, filtered and evaporated. The residue was purified by thick layer chromatography over silica gel using n-hexane-ethyl acetate as a solvent.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. customthe organic layer separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by thick layer chromatography over silica gel

Sources & evidence

ORD record
ord-fca3b83d92c54f478e0a504231ccda5a
Source dataset
uspto-grants-1985_10
Patent number
US04546098

Reaction notes

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