TBAF tetrahydrofuran → 1alpha,3beta-Dihydroxy-17-(4-hydroxy-4-methyl-2-pentynyloxymethyl)androsta-5,7,16-triene

HRID 1792177Notes

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][CH2:30][C:31]#[C:32][C:33]([O:36][Si](CC)(CC)CC)([CH3:35])[CH3:34])[CH2:12][C@@H:11]([O:44][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][O:29][CH2:30][C:31]#[C:32][C:33]([OH:36])([CH3:35])[CH3:34])[CH2:12][C@@H:11]([OH:44])[CH2:10]1

Participants

Reactant 2

HCID 11078149TBAF tetrahydrofuran

HCID 696305781alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(4-triethylsilyloxy-4-methyl-2-pentynyloxymethyl)androsta-5,7,16-triene

Product 1

HCID 696296971alpha,3beta-Dihydroxy-17-(4-hydroxy-4-methyl-2-pentynyloxymethyl)androsta-5,7,16-trieneYield 92%

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(4-triethylsilyloxy-4-methyl-2-pentynyloxymethyl)androsta-5,7,16-triene (480 mg, 0.635 mmol) and 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (6 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (4 hours), worked up and purified by column chromatography (ethyl acetate:dichloromethane=4:1 followed by ethyl acetate) to give the titled compound (240 mg, 92%) as a pale yellow foam.

Workup

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

Sources & evidence

ORD record: ord-ade17ca973774d5a9b2f32830f0a6725
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074777B2

Reaction notes

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