Tetrabutylammonium Fluoride → HCID 12020096, compound

HRID 2268311Notes

Reaction equation

HRID 2268311 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][C@H:25]([OH:31])[CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:22])[CH2:12][C@@H:11]([O:39][Si](C(C)(C)C)(C)C)[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][C@H:25]([OH:31])[CH:26]([CH2:27][CH3:28])[CH2:29][CH3:30])[CH3:22])[CH2:12][C@@H:11]([OH:39])[CH2:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 12020094HCID 12020094, compound

Product 1

HCID 12020096HCID 12020096, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

By the same procedure as in Example 9, 1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-{3-ethyl-2(R)-hydroxypentyl-thio}pregna-5,7,16-triene (54.9 mg, 0.0797 mmol), tetrahydrofuran (3 ml) and 1M tetra-n-butylammonium fluoride solution in tetrahydrofuran (2 ml) were reacted (heating under reflux for 5 hours) and worked up, and then the residue was purified by preparative thin layer chromatography (0.5 mm×2, dichloromethane:ethanol=9:1, developed once) to give the title compound as a colorless oil (37.9 mg, 100%).

Workup

  1. temperature(heating under reflux for 5 hours)
  2. customthe residue was purified by preparative thin layer chromatography (0.5 mm×2, dichloromethane

Sources & evidence

ORD record
ord-8569722ee24340208b5e27a49e7668ef
Source dataset
uspto-grants-2001_12
Patent number
US06326503B1

Reaction notes

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