1alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17beta-{4-ethyl-4-(triethylsilyloxy)hexyloxymethyl}androsta-5,7-diene 4-phenyl-1,2,4-triazoline-3,5-dione → 1alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17beta-{4-ethyl-4-(triethylsilyloxy)hexyloxymethyl}androsta-5,7-diene

HRID 1792230Notes

Reaction equation

HRID 1792230 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][O:42][CH2:43][CH2:44][CH2:45][C:46]([CH2:57][CH3:58])([O:49][Si:50]([CH2:55][CH3:56])([CH2:53][CH3:54])[CH2:51][CH3:52])[CH2:47][CH3:48])[CH2:25][C@@H:24]([O:59][Si:60]([C:63]([CH3:66])([CH3:65])[CH3:64])([CH3:62])[CH3:61])[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][O:42][CH2:43][CH2:44][CH2:45][C:46]([CH2:57][CH3:58])([O:49][Si:50]([CH2:51][CH3:52])([CH2:55][CH3:56])[CH2:53][CH3:54])[CH2:47][CH3:48])[CH2:25][C@@H:24]([O:59][Si:60]([C:63]([CH3:64])([CH3:65])[CH3:66])([CH3:61])[CH3:62])[CH2:23]1)([C:17]([CH3:19])([CH3:18])[CH3:20])([CH3:16])[CH3:15]

Participants

3

Reactant 1

HCID 867601591alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17beta-{4-ethyl-4-(triethylsilyloxy)hexyloxymethyl}androsta-5,7-diene 4-phenyl-1,2,4-triazoline-3,5-dione

Product 1

HCID 696305921alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17beta-{4-ethyl-4-(triethylsilyloxy)hexyloxymethyl}androsta-5,7-dieneYield 48.9%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
140 °C

Procedure

After adding 1,3-dimethyl-2-imidazolidinone (10 ml) to 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-{4-ethyl-4-(triethylsilyloxy)hexyloxymethyl}androsta-5,7-diene 4-phenyl-1,2,4-triazoline-3,5-dione adduct (0.45 g), the mixture was heated to 140° C. and reaction was proceeded for 2 hours. The reaction mixture was cooled and 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 resulting residue was purified by column chromatography (hexane:ethyl acetate=40:1) to give the titled compound (0.18 g).

Workup

  1. customreaction
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with hexane
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe resulting residue was purified by column chromatography (hexane:ethyl acetate=40:1)

Sources & evidence

ORD record
ord-bec614065837464b94be9d7d2e47a0db
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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