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Water → 15beta,16beta-Methylene-3-methoxyandrosta-3,5-diene-17-one

HRID 1876737
Notes
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Reaction equation

HRID 1876737 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[OH-].[K+].C(O[C@@H:13]1[C@H:18]2[C@H:19]3[C@H:29]([CH2:30][CH2:31][C@:16]2([CH3:17])[C:15](=[O:34])[CH2:14]1)[C@:27]1([CH3:28])[C:22]([CH:23]=[C:24]([O:32][CH3:33])[CH2:25][CH2:26]1)=[CH:21][CH2:20]3)(=O)C.O>CS(C)=O>[CH2:2]1[C@@H:14]2[C:15](=[O:34])[C@:16]3([CH2:31][CH2:30][C@H:29]4[C@@H:19]([CH2:20][CH:21]=[C:22]5[C@:27]4([CH3:28])[CH2:26][CH2:25][C:24]([O:32][CH3:33])=[CH:23]5)[C@@H:18]3[C@H:13]12)[CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 54571005(15alpha)-15-(Acetyloxy)-3-methoxyandrosta-3,5-dien-17-one

Product 1

HCID 1403164815beta,16beta-Methylene-3-methoxyandrosta-3,5-diene-17-one

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
27.5 °C

Procedure

12.96 kg of trimethylsulfoxonium iodide is dissolved in 180 l of dimethyl sulfoxide under nitrogen bubbling and vigorous stirring and at 25-30° C. 5.51 kg of potassium hydroxide is added to the solution. Stirring is continued for 1 hour, then 16.22 kg of 15α-acetoxy-3-methoxyandrosta-3,5-diene-17-one is added, the reaction mixture is stirred at 25-30° C. until the reaction is complete (about 6 hours). The solution is added slowly to 900 l of water, the precipitate obtained is stirred for 30 minutes until it is dense, filtered by centrifuge, washed with portions of water until is neutral and dried in vacuo to constant weight at a temperature below 40° C. and the crude tide compound is crystallized from methanol.

Workup

  1. stirringStirring
  2. stirringthe reaction mixture is stirred at 25-30° C. until the reaction
  3. custom(about 6 hours)
  4. customthe precipitate obtained
  5. stirringis stirred for 30 minutes until it
  6. filtrationfiltered by centrifuge
  7. washwashed with portions of water
  8. customdried in vacuo to constant weight at a temperature below 40° C.
  9. customthe crude tide compound is crystallized from methanol

Sources & evidence

ORD record
ord-49ad37c4f9d043ebbf1a289c2e247868
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08309712B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes