Reaktion #67191

ord-7b3fc6a21f1f4934a8da492718571a53

Reaktionsgleichung

Cl
hydrochloric acid
Cc1ccc(S(=O)(=O)OC[C@H]2COc3ccc(S(=O)(=O)C(F)(F)F)cc3O2)cc1
[(2R)-7-(trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl-4-methylbenzenesulfonate
CCCN
propan-1-amine
→
CCCNC[C@H]1COc2ccc(S(=O)(=O)C(F)(F)F)cc2O1
N-{[(2S)-7-(TRIFLUOROMETHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL}PROPAN-1-AMINE

Edukte

Cl
hydrochloric acid
Cc1ccc(S(=O)(=O)OC[C@H]2COc3ccc(S(=O)(=O)C(F)(F)F)cc3O2)cc1
[(2R)-7-(trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl-4-methylbenzenesulfonate
CCCN
propan-1-amine
—
amine

Reagenzien

Keine

Lösungsmittel

CC#N
ACN

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePreparation
  2. 2
    Sonstigerecrystallized from acetonitrile
  3. 3
    Sonstige[α]=+50° (MeOH)

Vorschrift

Preparation according to Example 2 using [(2R)-7-(trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl-4-methylbenzenesulfonate (0.39 g, 0.98 mmol), propan-1-amine (1 ml) and ACN (2 ml). Yield: 0.150 g, 45%. The amine was converted to the hydrochloric acid salt and recrystallized from acetonitrile. M.p. 175° C. MS m/z (rel. intensity, 70 eV) 339 (M+, 2) 310 (10), 270 (6), 72 (bp), 70 (6). [α]=+50° (MeOH).

Quelle

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