HCID 14304771, compound → HCID 70300251, compound

HRID 399967Notes

Reaction equation

HRID 399967 reaction equation
CC(C)([O-:4])C.[K+].[Si:7]([O:14][C@@H:15]1[C@@:32]2([CH3:33])[C:19](=[CH:20][CH:21]=[C:22]3[C@@H:31]2[CH2:30][CH2:29][C@@:27]2([CH3:28])[C@H:23]3[CH2:24][CH2:25][C:26]2=[O:34])[CH2:18][C@@H:17]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:16]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>O1CCCC1>[Si:7]([O:14][C@@H:15]1[C@@:32]2([CH3:33])[C:19](=[CH:20][CH:21]=[C:22]3[C@@H:31]2[CH2:30][CH2:29][C@@:27]2([CH3:28])[C@H:23]3[CH2:24][C@@H:25]([OH:4])[C:26]2=[O:34])[CH2:18][C@@H:17]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:37])[CH3:38])[CH2:16]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 14304771HCID 14304771, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 70300251HCID 70300251, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Under an argon atmosphere, a solution of potassium t-butoxide (4.13 g, 36.8 mmol) in dry tetrahydrofuran (500 ml) was cooled to -78° C., and a solution of 1α,3β-bis(t-butyldimethylsilyloxy)-17-oxoandrosta-5,7-diene (13.0 g, 24.5 mmol) in tetrahydrofuran (40 ml) was added dropwise. After the mixture was stirred at the same temperature for 1 hour, a solution of 2-(phenylsulfonyl)-3-phenyloxazyldine (9.62 g, 36.8 mmol) in tetrahydrofuran (40 ml) was added dropwise and the mixture was further stirred at -78° C. for 1.5 hour. The reaction mixture was quenched with an aqueous saturated ammonium chloride solution, poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was concentrated under reduced pressure and the deposited solids were filtered, then the filtrate was concentrated again and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate:chloroform=7:1:2) to give the title compound as a white solid (3.10 g, 23%).

Workup

  1. stirringthe mixture was further stirred at -78° C. for 1.5 hour
  2. customThe reaction mixture was quenched with an aqueous saturated ammonium chloride solution
  3. additionpoured into water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe mixture was concentrated under reduced pressure
  8. filtrationthe deposited solids were filtered
  9. concentrationthe filtrate was concentrated again
  10. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate:chloroform=7:1:2)

Sources & evidence

ORD record
ord-a77630f7534e4147876b5d950526c1da
Source dataset
uspto-grants-1998_10
Patent number
US05824811

Reaction notes

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