Water → HCID 54230118, compound

HRID 1649336Notes

Reaction equation

HRID 1649336 reaction equation
[F:1][CH:2]([F:22])[C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:4]12[CH3:5])[C:17]1[CH2:16][CH2:15][C:14](=[O:21])[CH2:13][C:12]=1[CH2:11][CH2:10]3.C1C=C[NH+]=CC=1.Br[Br-]Br.O>N1C=CC=CC=1>[F:1][CH:2]([F:22])[C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C:18]([CH2:19][CH2:20][C@:4]12[CH3:5])=[C:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3

Participants

4

Reactant 2

HCID 962WaterHCID 57174879HCID 57174879, compound

Product 1

HCID 54230118HCID 54230118, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 17β-difluoromethylestr-5(10)-en-3-one is dissolved in pyridine under nitrogen with stirring. Pyridinium bromide perbromide is added over a 5-minute period. The reaction is stirred at 20°-25° under nitrogen for about 2.5 hr. Water is then added and the product extracted with diethyl ether. The diethyl ether extract is washed with water, dilute hydrochloric acid, water, dilute bicarbonate, water, and chromatographed over a silica gel column. The column is eluted with a gradient between 10% ethyl acetate-SSB and 60% ethyl acetate-SSB. The appropriate fractions are pooled and concentrated. The concentrate is rechromatographed and recrystallized from acetone to give the title compound.

Workup

  1. stirringThe reaction is stirred at 20°-25° under nitrogen for about 2.5 hr
  2. extractionthe product extracted with diethyl ether
  3. extractionThe diethyl ether extract
  4. washis washed with water, dilute hydrochloric acid, water, dilute bicarbonate, water
  5. customchromatographed over a silica gel column
  6. washThe column is eluted with a gradient between 10% ethyl acetate-SSB and 60% ethyl acetate-SSB
  7. concentrationconcentrated
  8. customThe concentrate is rechromatographed
  9. customrecrystallized from acetone

Sources & evidence

ORD record
ord-e171577971d74e3ab1c0e17f19c734d9
Source dataset
uspto-grants-1983_11
Patent number
US04416822

Reaction notes

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