Sodium cyanoborohydride → HCID 10688845, compound

HRID 618869Notes

Reaction equation

HRID 618869 reaction equation
[C:1]([O:4][C@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@H: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])[C@H: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 23238953HCID 23238953, compound

Product 1

HCID 10688845HCID 10688845, compoundYield 69.1%

Reagents, catalysts & solvents 3

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

Procedure

A solution of 27.4 g of 3β-acetoxy-5β-pregn-14-en-20-one (Bach, G. et al, Can J. Chem. 1968, 46, 733) and p-toluensulphonyl hydrazide (17.1 g) in AcOH (50 mL) was stirred at room temp. for 4 hrs. The solvent was evaporated to dryness under reduced pressure; the residue obtained was dissolved in MeOH (600 mL) and zinc iodide (3.0 g) was added. To this solution sodium cyanoborohydride (14.4 g) was added portionwise and the temperature was raised to the boiling point of the reaction mixture. After 4 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 95/5 as eluant to give 18.2 g of 3β-acetoxy-5β-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 4 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-a8285ab130984ed38f28fb73f675c2c4
Source dataset
uspto-grants-1999_09
Patent number
US05955632

Reaction notes

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