Reaktion #67286

ord-34253c481f544bc9a00407a9166f622c

Reaktionsgleichung

CS(=O)(=O)c1cc(F)c2c(c1)O[C@@H](CO)CO2
[(2S)-5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol
Cc1ccc(S(=O)(=O)Cl)cc1
p-toluenesulfonyl chloride
→
Cc1ccc(S(=O)(=O)OC[C@H]2COc3c(F)cc(S(C)(=O)=O)cc3O2)cc1
[(2R)-5-FLUORO-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL 4-METHYLBENZENESULFONATE

Edukte

—
( 26 )
—
( 50 )
—
TEA
CS(=O)(=O)c1cc(F)c2c(c1)O[C@@H](CO)CO2
[(2S)-5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol
Cc1ccc(S(=O)(=O)Cl)cc1
p-toluenesulfonyl chloride
—
( 19 )

Reagenzien

CN(C)c1ccncc1
4-DMAP

Lösungsmittel

ClCCl
DCM

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePreparation

Vorschrift

Preparation according to Preparation 10 using [[(2S)-5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (0.97 g, 3.7 mmol), DCM (20 ml), p-toluenesulfonyl chloride (1.06 g, 5.6 mmol), TEA (0.78 ml, 5.6 mmol) and 4-DMAP (0.46 g, 3.7 mmol). Yield: 1.47 g. MS m/z (rel. intensity, 70 eV) 416 (M+, 40), 244 (bp), 243 (26), 231 (19), 91 (50).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524766B2uspto-grants-2013_09