TBAF tetrahydrofuran → 1alpha,3beta-dihydroxy-20-{4-hydroxy-4-methyl-(2E)-pentenyloxy}-20-methylpregna-5,7,16-triene

HRID 1792186Notes

Reaction equation

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

Participants

Reactant 2

HCID 11078149TBAF tetrahydrofuran

HCID 867601421alpha,3beta-bis(tert-butyldimethylsilyloxy)-20-{4-triethylsilyloxy-4-methyl-(2E)-pentenyloxy}-20-methylpregna-5,7,16-triene

Product 1

HCID 867601431alpha,3beta-dihydroxy-20-{4-hydroxy-4-methyl-(2E)-pentenyloxy}-20-methylpregna-5,7,16-trieneYield 97%

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-20-{4-triethylsilyloxy-4-methyl-(2E)-pentenyloxy}-20-methylpregna-5,7,16-triene (136 mg, 0.173 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 (74 mg, 97%) as a colorless foam.

Workup

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

Sources & evidence

ORD record: ord-b4693b8165144b8c92ddf32fa3d251c5
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074777B2

Reaction notes

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