Reaktion #67175

ord-e4934b19b2bd48b7bd8265b719dcc552

Reaktionsgleichung

Cc1ccc(S(=O)(=O)OC[C@H]2COc3ccc(S(C)(=O)=O)cc3O2)cc1
[(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate
CCN
ethanamine
→
CCNC[C@H]1COc2ccc(S(C)(=O)=O)cc2O1
N-{[(2S)-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL}ETHANAMINE

Edukte

Cc1ccc(S(=O)(=O)OC[C@H]2COc3ccc(S(C)(=O)=O)cc3O2)cc1
[(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate
CCN
ethanamine

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) and flash column chromatography (Isooctane/EtOAc/MeOH)
  2. 2
    Sonstigecrystallized from MeOH/Et2O
  3. 3
    Sonstige[α]=−66° (MeOH)

Vorschrift

A mixture of [(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (1.0 g, 2.51 mmol), ethanamine (2 ml, 70% in water) and ACN (6 ml) was heated under microwave radiation at 120° C. for 20 min. Purification on SCX-3 column (TEA/MeOH) and flash column chromatography (Isooctane/EtOAc/MeOH). Yield: 0.53 g, 78%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 271° C. MS m/z (rel. intensity, 70 eV) 271 (M+, 29), 58 (100), 59 (10), 272 (7), 79 (5). [α]=−66° (MeOH).

Quelle

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