Tetrabutylammonium Fluoride → 1alpha,3beta-Dihydroxy-20(S)-(3-ethyl-3hydroxypentylthio)pregna-5,7,16-triene

HRID 635023Notes

Reaction equation

HRID 635023 reaction equation
[Si]([O:8][C@@H:9]1[C@@:36]2([CH3:37])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:38])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([S:23][CH2:24][CH2:25][C:26]([CH2:30][CH3:31])([OH:29])[CH2:27][CH3:28])[CH3:22])[CH2:12][C@@H:11]([OH:39])[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C@@H:9]1[C@@:36]2([CH3:37])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:38])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([S:23][CH2:24][CH2:25][C:26]([CH2:30][CH3:31])([OH:29])[CH2:27][CH3:28])[CH3:22])[CH2:12][C@@H:11]([OH:39])[CH2:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 120195171alpha-(tert-butyldimethylsilyloxy)-3beta-hydroxy-20(S)-(3-ethyl-3-hydroxypentylthio)pregna-5,7,16-triene

Product 1

HCID 120195231alpha,3beta-Dihydroxy-20(S)-(3-ethyl-3hydroxypentylthio)pregna-5,7,16-trieneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under the same conditions as in Example 9, the crude 1α-(tert-butyldimethylsilyloxy)-3β-hydroxy-20(S)-(3-ethyl-3-hydroxypentylthio)pregna-5,7,16-triene obtained in Example 7, tetrahydrofuran (2 ml) and 1M tetra-n-butylammonium fluoride solution in tetrahydrofuran (2 ml) were reacted and worked up, and then the residue was purified by preparative thin layer chromatography (0.5 mm×2, dichloromethane:ethanol =7:1, developed once) to give the title compound as a colorless oil (42.0 mg, 64%, 2 steps).

Workup

  1. customthe residue was purified by preparative thin layer chromatography (0.5 mm×2, dichloromethane

Sources & evidence

ORD record
ord-0500cc41d2254b8883d2a0a777af236e
Source dataset
uspto-grants-2001_02
Patent number
US06184398B2

Reaction notes

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