TBAF tetrahydrofuran → 17-{4-Ethyl-4-hydroxy-(2e)-hexenyloxymethyl}1alpha,3beta-dihydroxyandrosta-5,7,16-triene

HRID 1792180Notes

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][O:29]/[CH:30]=[CH:31]/[CH2:32][C:33]([CH2:44][CH3:45])([O:36][Si](CC)(CC)CC)[CH2:34][CH3:35])[CH2:12][C@@H:11]([O:46][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH2:34]([C:33]([OH:36])([CH2:44][CH3:45])[CH2:32]/[CH:31]=[CH:30]/[O:29][CH2:28][C:20]1[C@:21]2([CH2:23][CH2:24][C@H:25]3[C:16](=[CH:15][CH:14]=[C:13]4[C@:26]3([CH3:27])[C@@H:9]([OH:8])[CH2:10][C@H:11]([OH:46])[CH2:12]4)[C@@H:17]2[CH2:18][CH:19]=1)[CH3:22])[CH3:35]

Participants

Reactant 2

HCID 11078149TBAF tetrahydrofuran

HCID 131725856HCID 131725856, compound

Product 1

HCID 13172585517-{4-Ethyl-4-hydroxy-(2e)-hexenyloxymethyl}1alpha,3beta-dihydroxyandrosta-5,7,16-trieneYield 73%

Procedure

The mixture (540 mg) containing the 1α,3β-bis(tert-butyldimethylsilyloxy)-17-{4-ethyl-4-triethylsilyloxy-(2E)-hexenyloxymethyl}androsta-5,7,16-triene obtained in Example 10(1) and a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (7 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (3 hours), worked up and purified by column chromatography (dichloromethane:ethyl acetate=1:4) to give the titled compound (222 mg, 73%) as a white foam.

Workup

customof Example 5(2) (3 hours)
custompurified by column chromatography (dichloromethane:ethyl acetate=1:4)

Sources & evidence

ORD record: ord-e7a2520a1c4a4c4dae10fd9bba6e0c39
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074777B2

Reaction notes

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