Tetrabutylammonium Fluoride → (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-Hexahydro-6-hydroxy-8-[(2RS)-2-(2-methylphenoxy)-2-methylvaleryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one

HRID 2396197Notes

Reaction equation

HRID 2396197 reaction equation
[Si]([O:8][C@H:9]1[CH2:18][C@H:17]([O:19][C:20](=[O:34])[C:21]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])([CH3:25])[CH2:22][CH2:23][CH3:24])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:52])[C@@H:15]2[CH2:35][CH2:36][C@H:37]2[O:42][C:41](=[O:43])[CH2:40][C@H:39]([O:44][Si](C(C)(C)C)(C)C)[CH2:38]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:34])[C:21]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])([CH3:25])[CH2:22][CH2:23][CH3:24])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:52])[C@@H:15]2[CH2:35][CH2:36][C@H:37]2[O:42][C:41](=[O:43])[CH2:40][C@H:39]([OH:44])[CH2:38]2)=[CH:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 56977077(4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-Hexahydro-6-t-butyldimethylsilyloxy-8-[(2RS)-2-(2-methylphenoxy)-2-methylvaleryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one

Product 1

HCID 54111790(4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-Hexahydro-6-hydroxy-8-[(2RS)-2-(2-methylphenoxy)-2-methylvaleryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-hydroxy-2H-pyran-2-oneYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Example 2, above, was followed, but using 0.35 g of (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-hexahydro-6-t-butyldimethysilyloxy-8-[(2RS)-2-(2-methylphenoxy)-2-methylvaleryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example 76, above] and 11.1 ml of a 1.0 molar solution of tetrabutylammonium fluoride in tetrahydrofuran, to give 0.16 g of the title compound as white crystals, melting at between 161° and 163° C.

Sources & evidence

ORD record
ord-75aa8050dab64392aaea036964dfabb9
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

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