Reaktion #67172

ord-0c367b480992494aa92191ac61b3673b

Reaktionsgleichung

Cc1ccc(S(=O)(=O)OC[C@@H]2COc3ccc(S(C)(=O)=O)cc3O2)cc1
[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate
CCCN
propan-1-amine
→
CCCNC[C@@H]1COc2ccc(S(C)(=O)=O)cc2O1
N-{[(2R)-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
[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate
CCCN
propan-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 (EtOAc/MeOH)
  2. 2
    Sonstigecrystallized from MeOH/Et2O
  3. 3
    Sonstige[α]=+67° (MeOH)

Vorschrift

A mixture of [(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.7 g, 1.8 mmol), propan-1-amine (1 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 (EtOAc/MeOH). Yield: 0.4 g, 73%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 228° C. MS m/z (rel. intensity, 70 eV) 285 (M+, 3), 207 (4), 73 (5), 72 (bp), 70 (5). [α]=+67° (MeOH).

Quelle

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