Tetrabutylammonium Fluoride → HCID 54002040, compound

HRID 2396177Notes

Reaction equation

HRID 2396177 reaction equation
[Si]([O:8][C@H:9]1[CH2:18][C@H:17]([O:19][C:20](=[O:31])[CH:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:22][CH3:23])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:49])[C@@H:15]2[CH2:32][CH2:33][C@H:34]2[O:39][C:38](=[O:40])[CH2:37][C@H:36]([O:41][Si](C(C)(C)C)(C)C)[CH2:35]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:31])[CH:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:22][CH3:23])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:49])[C@@H:15]2[CH2:32][CH2:33][C@H:34]2[O:39][C:38](=[O:40])[CH2:37][C@H:36]([OH:41])[CH2:35]2)=[CH:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54544559HCID 54544559, compound

Product 1

HCID 54002040HCID 54002040, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Example above, was followed, but using 1.10 g of (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-[(2RS)-2-phenoxybutyryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example 37, above] and 37.7 ml of a 1.0 molar solution of tetrabutylammonium fluoride in tetrahydrofuran, to give 0.29 g of the title compound as whitecrystals, melting at between 120° and 122° C.

Sources & evidence

ORD record
ord-81c0a29cc3414989a09dd0a7260abe0a
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

Loading…