TBAF tetrahydrofuran → 1alpha,3beta-Dihydroxy-17-(5-hydroxy-5-methylhexylthiomethyl)androsta-5,7,16-triene

HRID 1792216Notes

Reaction equation

[Si]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH:19]=[C:20]2[CH2:28][S:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:37][Si](CC)(CC)CC)([CH3:36])[CH3:35])[CH2:12][C@@H:11]([O:45][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[OH:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH:19]=[C:20]2[CH2:28][S:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:37])([CH3:36])[CH3:35])[CH2:12][C@@H:11]([OH:45])[CH2:10]1

Participants

Reactant 2

HCID 11078149TBAF tetrahydrofuran

HCID 696297051alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(5-triethylsilyloxy-5-methylhexylthiomethyl)androsta-5,7,16-triene

Product 1

HCID 696302111alpha,3beta-Dihydroxy-17-(5-hydroxy-5-methylhexylthiomethyl)androsta-5,7,16-trieneYield 86%

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(5-triethylsilyloxy-5-methylhexylthiomethyl)androsta-5,7,16-triene (313 mg, 0.396 mmol) and a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (5 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (3 hours), worked up and purified by column chromatography (ethyl acetate) to give the titled compound (152 mg, 86%) as a colorless solid.

Workup

customof Example 5(2) (3 hours)
custompurified by column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-b41b6eb811fc48af8c53214cc8ff7762
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074777B2

Reaction notes

Loading…