TBAF tetrahydrofuran → 1alpha,3beta-Dihydroxy-17-(3-hydroxy-3-methylbutylthiomethyl)androsta-5,7,16-triene

HRID 1792220Notes

Reaction equation

HRID 1792220 reaction equation
[Si]([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][S:29][CH2:30][CH2:31][C:32]([OH:35])([CH3:34])[CH3:33])[CH2:12][C@@H:11]([O:36][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH: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][S:29][CH2:30][CH2:31][C:32]([OH:35])([CH3:34])[CH3:33])[CH2:12][C@@H:11]([OH:36])[CH2:10]1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 696298861alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(3-hydroxy-3-methylbutylthiomethyl)androsta-5,7,16-triene

Product 1

HCID 696305961alpha,3beta-Dihydroxy-17-(3-hydroxy-3-methylbutylthiomethyl)androsta-5,7,16-trieneYield 95.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(3-hydroxy-3-methylbutylthiomethyl)androsta-5,7,16-triene (63.5 mg, 0.0981 mmol), a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (1 ml) and tetrahydrofuran (1 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (reflux under heating for 5.5 hours), worked up and purified by preparative thin layer chromatography (2 sheets (each 0.5 mm thickness), dichloromethane:ethanol=9:1, developed once) to give the titled compound (39.2 mg, 95%) as a colorless oil.

Workup

  1. temperatureof Example 5(2) (reflux under heating for 5.5 hours)
  2. custompurified by preparative thin layer chromatography (2 sheets (each 0.5 mm thickness), dichloromethane

Sources & evidence

ORD record
ord-5ee07af8e70c4954abdedabfc16b7f64
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

Loading…