Sodium hydride → 1alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(5-triethylsilyloxy-5-methylhexyloxymethyl)androsta-5,7,16-triene

HRID 1792174Notes

Reaction equation

HRID 1792174 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH:19]=[C:20]2[CH2:28][OH:29])[CH2:12][C@@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:46][Si:47]([CH2:52][CH3:53])([CH2:50][CH3:51])[CH2:48][CH3:49])([CH3:45])[CH3:44].[H-].[Na+].C1OCCOCCOCCOCCOC1>O1CCCC1>[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH:19]=[C:20]2[CH2:28][O:29][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:46][Si:47]([CH2:52][CH3:53])([CH2:48][CH3:49])[CH2:50][CH3:51])([CH3:45])[CH3:44])[CH2:12][C@@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 220168031-Bromo-5-triethylsilyloxy-5-methylhexaneHCID 673014381alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene

Product 1

HCID 696301211alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(5-triethylsilyloxy-5-methylhexyloxymethyl)androsta-5,7,16-trieneYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (200 mg, 0.367 mmol), 1-bromo-5-triethylsilyloxy-5-methylhexane (227 mg, 0.734 mmol), sodium hydride (60% in oil, 44 mg, 1.10 mmol), 15-crown-5 (81 mg, 0.368 mmol) and tetrahydrofuran (0.5 ml) were subjected to reaction using a procedure similar to that of Example 5(1) (reflux under heating for 1 hour), worked up and purified by column chromatography (hexane:toluene=3:2) to give the titled compound (270 mg, 95%) as a colorless oil.

Workup

  1. temperatureof Example 5(1) (reflux under heating for 1 hour)
  2. custompurified by column chromatography (hexane:toluene=3:2)

Sources & evidence

ORD record
ord-51ebe64bd2154f2b9412ca6ccc7b36e4
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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