TBAF tetrahydrofuran → HCID 69630492, compound

HRID 1792206Notes

Reaction equation

HRID 1792206 reaction equation
[Si]([O:8][C@@H:9]1[C@@:37]2([CH3:38])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([O:24][CH2:25][CH2:26][C:27]([CH2:31][CH3:32])([OH:30])[CH2:28][CH3:29])([CH3:23])[CH3:22])[CH2:12][C@@H:11]([O:40][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@@:37]2([CH3:38])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([O:24][CH2:25][CH2:26][C:27]([CH2:28][CH3:29])([OH:30])[CH2:31][CH3:32])([CH3:23])[CH3:22])[CH2:12][C@@H:11]([OH:40])[CH2:10]1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 69629895HCID 69629895, compound

Product 1

HCID 69630492HCID 69630492, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-20-(3-ethyl-3-hydroxypentyloxy)-20-methylpregna-5,7,16-triene (85 mg, 0.12 mmol), a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (1.2 ml) and tetrahydrofuran (4.6 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (3 hours), worked up and purified by preparative thin layer chromatography (3 sheets (each 0.5 mm thickness), ethyl acetate:dichloromethane=4:1) to give the titled compound (55 mg, 100%) as a colorless oil.

Workup

  1. customof Example 5(2) (3 hours)
  2. custompurified by preparative thin layer chromatography (3 sheets (each 0.5 mm thickness), ethyl acetate

Sources & evidence

ORD record
ord-4f1ca6185ce24e27b5c2376a8ade2ba8
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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