HCID 22875683, compound → HCID 22875682, compound

HRID 362797Notes

Reaction equation

HRID 362797 reaction equation
[Si:1]([O:8][CH:9]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:18]([CH2:19][CH:20]([OH:30])[CH2:21][CH2:22]2)=[CH:17][C:16]3([CH3:32])O)[CH2:13][CH2:12]1)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.C1(=O)CCCCC1>[Si:1]([O:8][CH:9]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH:17]=[C:16]3[CH3:32])[CH2:13][CH2:12]1)[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 22875683HCID 22875683, compound2×

Product 1

HCID 22875682HCID 22875682, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7967CyclohexanoneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 20-tert-butyldimethylsilyloxy-7-methyl-pregn-5-ene-3,7-diol (298 gm, 0.59 mol, product of Step 4) in toluene (3 L) and cyclohexanone (1.03 L) was azeotroped to remove 750 mL of solvent. A solution of aluminum isopropoxide (121 gm) in toluene (620 mL) was added and the solution azeotroped to remove another 650 mL of solvent. A reflux condenser was added and the solution refluxed overnight. The solution was cooled to 40° C. and Supercell™ (125 gm) and water (125 mL) were added. After stirring for 10 min, the mixture was filtered and the solids washed with toluene (550 mL). The solvent was removed by rotoevaporation to yield a orange liquid which was purified by column chromatography on silica gel eluted with hexane, followed by 5-10% ethyl acetate in hexanes. The title compound was isolated as a mixture of 20α- and 20β-isomers.

Workup

  1. customto remove 750 mL of solvent
  2. additionA solution of aluminum isopropoxide (121 gm) in toluene (620 mL) was added
  3. customthe solution azeotroped
  4. customto remove another 650 mL of solvent
  5. additionA reflux condenser was added
  6. temperaturethe solution refluxed overnight
  7. additionSupercell™ (125 gm) and water (125 mL) were added
  8. filtrationthe mixture was filtered
  9. washthe solids washed with toluene (550 mL)
  10. customThe solvent was removed by rotoevaporation
  11. customto yield a orange liquid which
  12. customwas purified by column chromatography on silica gel
  13. washeluted with hexane

Sources & evidence

ORD record
ord-e118bbea7bf64d00b4e156f801bad79b
Source dataset
uspto-grants-1999_02
Patent number
US05872126

Reaction notes

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