Sodium cyanoborohydride → HCID 53852576, compound

HRID 618871Notes

Reaction equation

HRID 618871 reaction equation
[C:1]([O: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:11]3=[CH:12][CH2:13][C@@H:14]2[C:15](=O)[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].C([BH3-])#N.[Na+]>CC(O)=O.CO.[I-].[Zn+2].[I-]>[C:1]([O: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:11]3=[CH:12][CH2:13][C@@H:14]2[CH2:15][CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 53974580HCID 53974580, compound

Product 1

HCID 53852576HCID 53852576, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 9883512zinc(II)iodideCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 5.2 g of 3β-acetoxy-pregn-14-en-20-one (Gambara, T. et al, Chem. Pharm. Bull., 1970, 18, 453) and p-toluensulphonyl hydrazide (3.5 g) in AcOH (50 mL) was stirred at room temp. for 3 hrs. The solvent was evaporated to dryness under reduced pressure: the residue obtained was dissolved in MeOH (200 mL) and zinc iodide (0.6 g) was added. To this solution sodium cyanoborohydride (1.5 g) was added portionwise and the temperature was raised to the boiling point of the reaction mixture. After 2 hrs the solvent was evaporated to dryness under reduced pressure, the crude product was dissolved in ethyl acetate and neutralised with 0.1 N NaOH; the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 97/3 as eluant to give 3.7 g of 3β-acetoxy-pregn-14-ene as a white solid.

Workup

  1. customThe solvent was evaporated to dryness under reduced pressure
  2. customthe residue obtained
  3. temperaturethe temperature was raised to the boiling point of the reaction mixture
  4. customAfter 2 hrs the solvent was evaporated to dryness under reduced pressure
  5. dissolutionthe crude product was dissolved in ethyl acetate and neutralised with 0.1 N NaOH
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-4ed2d6d6bdf045a1932235828eaa1923
Source dataset
uspto-grants-1999_09
Patent number
US05955632

Reaction notes

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