Potassium Carbonate → HCID 70048161, compound

HRID 618870Notes

Reaction equation

HRID 618870 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:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO.O>[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:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23238953HCID 23238953, compound

Product 1

HCID 70048161HCID 70048161, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 10.0 g of 3β-acetoxy-5β-pregn-14-en-20-one (Bach, G. et al. Can. J. Chem. 1968, 46, 733) and K2CO3 (25.0 g) in MeOH/water (160 mL/80 mL) was stirred at room temperature for 2 hrs; the organic solvent was evaporated to dryness under reduced pressure and the aqueous suspension obtained was extracted with CH2Cl2 ; the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure; the crude 3β-acetoxy-5β,17α-pregn-14-en-20-one obtained was used for the next step without further purification. A solution of the crude intermediate and p-toluensulphonyl hydrazide (11.1 g) in AcOH (300 mL) was stirred at room temp. for 12 hrs. To this solution NaBH4 (7.8 g) was added portionwise; after 2 hrs the reaction mixture was poured in water/ice and the aqueous suspension obtained was extracted with AcOEt 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 1/1 as eluant to give 7.0 g of 3β-acetoxy-5β,17α-pregn-14-ene as a white solid.

Workup

  1. customthe organic solvent was evaporated to dryness under reduced pressure
  2. customthe aqueous suspension obtained
  3. extractionwas extracted with CH2Cl2
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8aaf24e7b2f54ea98d59a283c7f265f9
Source dataset
uspto-grants-1999_09
Patent number
US05955632

Reaction notes

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