Tetrabutylammonium Fluoride → 1alpha,3beta-dihydroxy-20(S)-(5-hydroxy-5-methylhexylthio)pregna-5,7,16-triene

HRID 2268294Notes

Reaction equation

HRID 2268294 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][CH2:26][CH2:27][C:28]([OH:31])([CH3:30])[CH3:29])[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][CH2:26][CH2:27][C:28]([OH:31])([CH3:30])[CH3:29])[CH3:22])[CH2:12][C@@H:11]([OH:39])[CH2:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 120195151alpha-(tert-Butyldimethylsilyloxy)-3beta-hydroxy-20(S)-(5-hydroxy-5-methyihexylthio)pregna-5,7,16-triene

Product 1

HCID 120195211alpha,3beta-dihydroxy-20(S)-(5-hydroxy-5-methylhexylthio)pregna-5,7,16-trieneYield 61.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under the same conditions as in Example 9, the crude 1α-(tert-butyldimethylsilyloxy)-3β-hydroxy-20(S)-(5-hydroxy-5-methylhexylthio)pregna-5,7,16-triene (73.2 mg) obtained in Example 5, 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 pale yellow oil (36.1 mg, 55%, 2 steps).

Workup

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

Sources & evidence

ORD record
ord-84cdca99ac0041a3a02cac3e60ec73b0
Source dataset
uspto-grants-2001_12
Patent number
US06326503B1

Reaction notes

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