Tetrabutylammonium Fluoride → HCID 54448649, compound

HRID 2396184Notes

Reaction equation

HRID 2396184 reaction equation
[Si]([O:8][C@H:9]1[CH2:18][C@H:17]([O:19][C:20](=[O:32])[CH:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[CH2:22][CH3:23])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:50])[C@@H:15]2[CH2:33][CH2:34][C@H:35]2[O:40][C:39](=[O:41])[CH2:38][C@H:37]([O:42][Si](C(C)(C)C)(C)C)[CH2:36]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:32])[CH:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[CH2:22][CH3:23])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:50])[C@@H:15]2[CH2:33][CH2:34][C@H:35]2[O:40][C:39](=[O:41])[CH2:38][C@H:37]([OH:42])[CH2:36]2)=[CH:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67677124HCID 67677124, compound

Product 1

HCID 54448649HCID 54448649, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Example 2, above, was followed, but using 1.26 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-fluorophenoxy)butyryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described inExample 55, above] and 25.9 ml of a 1.0 molar solution of tetrabutylammonium fluoride in tetrahydrofuran, to give 635 mg of the title compound as white crystals, melting at between 136° and 138° C.

Sources & evidence

ORD record
ord-8e00a3027ca04dffbb753d6b98cd081e
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

Loading…