Reaktion #67259

ord-258b468f1594451faaed443785c6be7a

Reaktionsgleichung

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
C1COCCN1
morpholine
→
CS(=O)(=O)c1cc(F)c2c(c1)O[C@@H](CN1CCOCC1)CO2
4-{[(S)-5-FLUORO-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL}MORPHOLINE

Edukte

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
C1COCCN1
morpholine

Reagenzien

Keine

Lösungsmittel

CC#N
ACN

Reaktionsbedingungen

Temperatur
120°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePurification on SCX-3 column (TEA/MeOH)
  2. 2
    Sonstigecrystallized from MeOH/Et2O

Vorschrift

A mixture of [(2R)-5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.39 g, 0.95 mmol), morpholine (0.3 ml, 3.4 mmol) and ACN (3 ml) was heated under microwave radiation at 120° C. for 70 min. Purification on SCX-3 column (TEA/MeOH) and by flash column chromatography and (isooctane/EtOAc/MeOH). Yield: 0.17 g. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 251° C. MS m/z (rel. intensity, 70 eV) 331 (M+, 1), 207 (2), 101 (6), 100 (bp), 69 (2), 56 (5).

Quelle

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