HCID 22875686, compound → HCID 22875683, compound

HRID 362796Notes

Reaction equation

HRID 362796 reaction equation
C([O:4][CH:5]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C:7](=[CH:8][C:9](=[O:34])[C@@H:10]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:33])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:15]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH3:16])[CH2:6]1)(=O)C.[CH3:35][Mg]Cl>O1CCCC1>[Si:18]([O:17][CH:15]([C@@H:14]1[C@:25]2([CH3:33])[C@H:11]([C@H:10]3[C@H:28]([CH2:27][CH2:26]2)[C@:29]2([CH3:32])[C:7]([CH2:6][CH:5]([OH:4])[CH2:31][CH2:30]2)=[CH:8][C:9]3([CH3:35])[OH:34])[CH2:12][CH2:13]1)[CH3:16])([C:21]([CH3:23])([CH3:22])[CH3:24])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 22875686HCID 22875686, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 22875683HCID 22875683, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-acetoxy-20-tert-butyldimethylsilyloxy-pregn-5-en-7-one (279 gm, 0.57 mol, product of Step 3) in tetrahydrofuran (5.6 L) was cooled to 4° C. A 3M solution of methyl magnesium chloride in tetrahydrofuran (1.037 L, 3.1 mol) was added at such a rate as to keep the temperature 0° C. The ice bath was removed and the reaction allowed to warm to room temperature overnight. The reaction was cooled in an ice bath and quenched with a 20% solution of ammonium chloride (3 L). The organic layer was removed and the aqueous layer extracted with ethyl acetate. The organic layers were combined, washed with saturated salt solution, and dried over anhydrous magnesium sulfate. The solution was filtered through a pad of anhydrous sodium sulfate and the solvent removed by rotoevaporation to yield the title compound.

Workup

  1. customthe temperature 0° C
  2. customThe ice bath was removed
  3. temperatureThe reaction was cooled in an ice bath
  4. customquenched with a 20% solution of ammonium chloride (3 L)
  5. customThe organic layer was removed
  6. extractionthe aqueous layer extracted with ethyl acetate
  7. washwashed with saturated salt solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationThe solution was filtered through a pad of anhydrous sodium sulfate
  10. customthe solvent removed by rotoevaporation

Sources & evidence

ORD record
ord-d753deb40e024ee5984a0da290334a80
Source dataset
uspto-grants-1999_02
Patent number
US05872126

Reaction notes

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