Tetrabutylammonium Fluoride → HCID 54175600, compound

HRID 2396229Notes

Reaction equation

HRID 2396229 reaction equation
[Si]([O:8][C@H:9]1[CH2:18][C@H:17]([O:19][C:20](=[O:36])[CH:21]([O:28][C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:54])[C@@H:15]2[CH2:37][CH2:38][C@H:39]2[O:44][C:43](=[O:45])[CH2:42][C@H:41]([O:46][Si](C(C)(C)C)(C)C)[CH2:40]2)=[CH:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C@H:9]1[CH2:18][C@H:17]([O:19][C:20](=[O:36])[CH:21]([O:28][C:29]2[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:54])[C@@H:15]2[CH2:37][CH2:38][C@H:39]2[O:44][C:43](=[O:45])[CH2:42][C@H:41]([OH:46])[CH2:40]2)=[CH:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54011443HCID 54011443, compound

Product 1

HCID 54175600HCID 54175600, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Example 2, above, was followed, but using 0.42 g of (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-[(2RS)-2-(4-methylphenoxy)-2-phenylacetoxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example 142, above] and 8.1 ml of a 1.0 molar solution of tetrabutylammonium fluoride in tetrahydrofuran, to give 220 mg of the title compound as a white powder, melting at between 130° and 133° C.

Sources & evidence

ORD record
ord-b49e36d15b7f464891705cca3b03d3c2
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

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