Reaktion #67184

ord-cfbb3531158c48fc852fede59e0efdef

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
CC(C)CN
2-methylpropane-1-amine
→
CC(C)CNC[C@H]1COc2ccc(S(C)(=O)=O)cc2O1
2-METHYL-N-{[(2S)-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL}PROPAN-1-AMINE

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
CC(C)CN
2-methylpropane-1-amine

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 (DCM/MeOH)
  2. 2
    Sonstigecrystallized from MeOH/Et2O
  3. 3
    Sonstige[α]=−58° (MeOH)

Vorschrift

A mixture of [(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.19 g, 0.48 mmol), 2-methylpropane-1-amine (0.9 ml) and ACN (3 ml) was heated under microwave radiation at 120° C. for 20 min. Purification on SCX-3 column (TEA/MeOH) and flash column chromatography (DCM/MeOH). Yield: 0.11 g, 74%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 214° C. MS m/z (rel. intensity, 70 eV) 299 (M+, 6), 86 (100), 256 (21), 57 (8), 70 (6). [α]=−58° (MeOH).

Quelle

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