Water → (15alpha,16alpha)-15,16-Dihydro-3-methoxy-3′H-cycloprop[15,16]androsta-3,5,15-trien-17-one

HRID 1876737Notes

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]

Participants

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

stirringStirring
stirringthe reaction mixture is stirred at 25-30° C. until the reaction
custom(about 6 hours)
customthe precipitate obtained
stirringis stirred for 30 minutes until it
filtrationfiltered by centrifuge
washwashed with portions of water
customdried in vacuo to constant weight at a temperature below 40° C.
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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