Tetrabutylammonium Fluoride → 2-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(2-hydroxyethoxy)hexyl]-, (5R)-

HRID 218995Notes

Reaction equation

[Si]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:22][C@@H:21]([C:23]2[CH:34]=[CH:33][C:26]3[O:27][C:28]([CH3:32])([CH3:31])[O:29][CH2:30][C:25]=3[CH:24]=2)[O:20][C:19]1=[O:35])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:31][C:28]1([CH3:32])[O:27][C:26]2[CH:33]=[CH:34][C:23]([C@H:21]3[O:20][C:19](=[O:35])[N:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][OH:8])[CH2:22]3)=[CH:24][C:25]=2[CH2:30][O:29]1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of (5R)-3-[6-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (0.79 g) in THF (30 ml) was treated with tetrabutylammonium fluoride on silica gel (3.08 g) and the mixture stirred under nitrogen at 20° C. for 2.75 h. The reaction mixture was filtered and the filtrate evaporated in vacuo to give a residue which was purified by SPE on silica. Elution with dichloromethane, then EtOAc followed by solvent evaporation in vacuo gave the title compound (0.56 g). LCMS RT=3.05 min, ES+ve 394 (MH)+.

Workup

filtrationThe reaction mixture was filtered
customthe filtrate evaporated in vacuo
customto give a residue which
customwas purified by SPE on silica
washElution with dichloromethane
customEtOAc followed by solvent evaporation in vacuo

Sources & evidence

ORD record: ord-44916f30ddb746e3baf00fb121846aa6
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198483B2

Reaction notes

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