TBAF tetrahydrofuran → 1alpha,3beta-Dihydroxy-20-(4-ethyl-4-hydroxyhexyloxy)-20-methylpregna-5,7,16-triene

HRID 1792182Notes

Reaction equation

[Si]([O:8][C@@H:9]1[C@@:45]2([CH3:46])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:44]2[CH2:43][CH2:42][C@@:41]2([CH3:47])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]([CH2:39][CH3:40])([O:31][Si](CC)(CC)CC)[CH2:29][CH3:30])([CH3:23])[CH3:22])[CH2:12][C@@H:11]([O:48][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@@:45]2([CH3:46])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:44]2[CH2:43][CH2:42][C@@:41]2([CH3:47])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]([CH2:39][CH3:40])([OH:31])[CH2:29][CH3:30])([CH3:22])[CH3:23])[CH2:12][C@@H:11]([OH:48])[CH2:10]1

Participants

Reactant 2

HCID 11078149TBAF tetrahydrofuran

HCID 696304291alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20-(4-ethyl-4-(triethylsilyloxy)hexyloxy)-20-methylpregna-5,7,16-triene

Product 1

HCID 696298831alpha,3beta-Dihydroxy-20-(4-ethyl-4-hydroxyhexyloxy)-20-methylpregna-5,7,16-trieneYield 100%

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-20-{4-ethyl-4-(triethylsilyloxy)hexyloxy}-20-methylpregna-5,7,16-triene (140 mg, 0.172 mmol) and a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (3 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 (81 mg, 100%) as a colorless foam.

Workup

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

Sources & evidence

ORD record: ord-e08e02393bac49fa91b78e613fcfa3d0
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074777B2

Reaction notes

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