TBAF tetrahydrofuran → HCID 86760141, compound

HRID 1792179Notes

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]([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]/[CH:30]=[CH:31]/[CH2:32][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 86760140HCID 86760140, compound

Product 1

HCID 86760141HCID 86760141, compoundYield 79.1%

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-17-{4-triethylsilyloxy-4-methyl-(2E)-pentenyloxymethyl}androsta-5,7,16-triene (550 mg, 0.726 mmol) 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) (4 hours), worked up and purified by column chromatography (using ethyl acetate:dichloromethane=4:1 and then ethyl acetate) to give the titled compound (238 mg, 79%) as a colorless foam.

Workup

customof Example 5(2) (4 hours)
custompurified by column chromatography (

Sources & evidence

ORD record: ord-1e6db17c0955403082c30ddc4ed71e35
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074777B2

Reaction notes

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