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

HRID 2396207Notes

Reaction equation

HRID 2396207 reaction equation
[Si]([O:8][C@H:9]1[CH2:18][C@H:17]([O:19][C:20](=[O:34])[CH:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31](=[O:33])[CH3:32])[CH2:22][CH3:23])[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])[CH:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31](=[O:33])[CH3:32])[CH2:22][CH3:23])[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 67730965(4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-Hexahydro-6-t-butyldimethylsilyloxy-8-[(2RS)-2-(2-acetylphenoxy)butyryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one

Product 1

HCID 67676249(4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-Hexahydro-6-hydroxy-8-[(2RS)-2-(2-acetylphenoxy)butyryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-hydroxy-2H-pyran-2-oneYield 43.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Example 2, above, was followed, but using 1.11 g of (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-[(2RS)-2-(2-acetylphenoxy)butyryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described inExample 97, above] and 35.3 ml of a 1.0 molar solution of tetrabutylammonium fluoride in tetrahydrofuran, to give 0.34 g of the title compound as white crystals, melting at between 148° and 150° C. Nuclear Magnetic Resonance Spectrum (270 MHz CDCl3) δ ppm: 1.10 (3H, triplet, J=7.3 Hz); 2.62 (3H, singlet); 4.32-4.52 (3H, multiplet); 4.81 (1H, triplet, J=5.9 Hz); 5.44 (1H, broad singlet); 5.52 (1H, broad singlet); 5.82 (1H, doublet of doublets, J=5.9 & 9.9 Hz); 5.93 (1H, doublet, J=9.9 Hz); 6.88 (1H, doublet, J=7.9 Hz); 7.00 (1H, triplet, J=8.6 Hz); 7.41 (1H, triplet, J=8.6 Hz); 7.72 (1H, doublet, J=7.9Hz).

Sources & evidence

ORD record
ord-244f1c2c8f3d4e8da4723ab49f4340ca
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

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