HCID 86760158, compound → HCID 69630335, compound

HRID 1792226Notes

Reaction equation

C1(N2C(=O)N=NC2=O)C=CC=CC=1.[Si:14]([O:21][C@@H:22]1[C@@:39]2([CH3:40])[C:26](=[CH:27][CH:28]=[C:29]3[C@@H:38]2[CH2:37][CH2:36][C@@:34]2([CH3:35])[C@H:30]3[CH2:31][CH2:32][C@@H:33]2[CH2:41][OH:42])[CH2:25][C@@H:24]([O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])[CH2:23]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN1CCN(C)C1=O>[Si:14]([O:21][C@@H:22]1[C@@:39]2([CH3:40])[C:26](=[CH:27][CH:28]=[C:29]3[C@@H:38]2[CH2:37][CH2:36][C@@:34]2([CH3:35])[C@H:30]3[CH2:31][CH2:32][C@@H:33]2[CH2:41][OH:42])[CH2:25][C@@H:24]([O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:45])[CH3:46])[CH2:23]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 140 °C

Procedure

To 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(hydroxymethyl)androsta-5,7-diene 4-phenyl-1,2,4-triazoline-3,5-dione adduct (6.3 g), was added 1,3-dimethyl-2-imidazolidinone (100 ml), followed by heating at 140° C. for 3 hours. The reaction mixture was extracted with hexane, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent. The thus obtained residue was purified by column chromatography (hexane:ethyl acetate=5:1) to give the titled compound (3.61 g).

Workup

extractionThe reaction mixture was extracted with hexane
washthe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customevaporated under reduced pressure
customto remove the solvent
customThe thus obtained residue was purified by column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-7e01337678114668953a6a702ba3c0c7
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074777B2

Reaction notes

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