Bromine → HCID 54274457, compound

HRID 1941182Notes

Reaction equation

HRID 1941182 reaction equation
[CH3:1][C@@H:2]1[C@:24]2([O:30][CH2:29][C@H:27]([CH3:28])[CH2:26][CH2:25]2)[O:23][C@H:4]2[CH2:5][C@@H:6]3[C@@:20]([CH3:21])([C@@H:3]12)[CH2:19][CH2:18][C@H:17]1[C@H:7]3[CH2:8][CH2:9][C@@H:10]2[C@:15]1([CH3:16])[CH2:14][CH2:13][C:12](=[O:22])[CH2:11]2.[Br:31]Br>O1CCCC1>[Br:31][C@@H:13]1[CH2:14][C@@:15]2([CH3:16])[C@@H:10]([CH2:9][CH2:8][C@@H:7]3[C@@H:17]2[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@H:6]3[CH2:5][C@@H:4]3[O:23][C@@:24]4([O:30][CH2:29][C@H:27]([CH3:28])[CH2:26][CH2:25]4)[C@@H:2]([CH3:1])[C@@H:3]32)[CH2:11][C:12]1=[O:22]

Participants

4

Reactant 2

HCID 24408BromineHCID 101692Spirostan-3-one

Product 1

HCID 54274457HCID 54274457, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of (5α,25R)-spirostan-3-one (1.00 g, 2.41 mmol) and tetrahydrofuran (10 mL) was cooled to -78° C. under nitrogen atmosphere. Bromine was added (0.39 g, 2.41 mmol) and the reaction mixture was gradually warmed to room temperature. After three hours, the reaction was quenched by the addition of saturated sodium bisulfite solution. The mixture was diluted with ethyl acetate, washed with saturated sodium bisulfite solution (1×), saturated sodium bicarbonate (1×), brine (1×), dried (sodium sulfate), filtered, and concentrated in vacuo, Upon addition of ether, a precipitate formed which was filtered and washed with hexanes to give 1.20 g, (85%) of the title compound.

Workup

  1. temperaturethe reaction mixture was gradually warmed to room temperature
  2. customthe reaction was quenched by the addition of saturated sodium bisulfite solution
  3. additionThe mixture was diluted with ethyl acetate
  4. washwashed with saturated sodium bisulfite solution (1×), saturated sodium bicarbonate (1×), brine (1×)
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo, Upon addition of ether
  8. customa precipitate formed which
  9. filtrationwas filtered
  10. washwashed with hexanes

Sources & evidence

ORD record
ord-e49b2936c9cd41769fff508cfc1b9a39
Source dataset
uspto-grants-1997_12
Patent number
US05703052

Reaction notes

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