TBAF tetrahydrofuran → 1alpha,3beta-Dihydroxy-20-(2-hydroxy-2-methylpropoxy)-20-methylpregna-5,7,16-triene

HRID 1792195Notes

Reaction equation

HRID 1792195 reaction equation
[Si]([O:8][C@@H:9]1[C@@:34]2([CH3:35])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:36])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([O:24][CH2:25][C:26]([OH:29])([CH3:28])[CH3:27])([CH3:23])[CH3:22])[CH2:12][C@@H:11]([O:37][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@@:34]2([CH3:35])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:36])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([O:24][CH2:25][C:26]([OH:29])([CH3:27])[CH3:28])([CH3:22])[CH3:23])[CH2:12][C@@H:11]([OH:37])[CH2:10]1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 696304801alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20-(2-hydroxy-2-methylpropoxy)-20-methylpregna-5,7,16-triene

Product 1

HCID 696299941alpha,3beta-Dihydroxy-20-(2-hydroxy-2-methylpropoxy)-20-methylpregna-5,7,16-trieneYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-20-(2-hydroxy-2-methylpropoxy)-20-methylpregna-5,7,16-triene (35.6 mg, 0.0552 mmol), a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (0.35 ml) and tetrahydrofuran (0.5 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (reflux under heating for 12 hours), worked up and the thus obtained residue was purified by preparative thin layer chromatography (1 sheet (0.5 mm thickness), dichloromethane:ethanol=15:1, developed three times) to give the titled compound (18.1 mg, 79%) as a colorless oil.

Workup

  1. temperatureof Example 5(2) (reflux under heating for 12 hours)
  2. customthe thus obtained residue was purified by preparative thin layer chromatography (1 sheet (0.5 mm thickness), dichloromethane:ethanol=15:1, developed three times)

Sources & evidence

ORD record
ord-abf3dd53ffae4780b6342c0773508a49
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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