Reaktion #67201

ord-d7c1de8f78f04b72ad9a62200bd3f331

Reaktionsgleichung

Cl
hydrochloric acid
Cc1ccc(S(=O)(=O)OC[C@H]2COc3c(Cl)cc(S(C)(=O)=O)cc3O2)cc1
[(2R)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate
CCN
ethanamine
→
CCNC[C@H]1COc2c(Cl)cc(S(C)(=O)=O)cc2O1
N-{[(2S)-5-CHLORO-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL}ETHANAMINE

Edukte

Cl
hydrochloric acid
Cc1ccc(S(=O)(=O)OC[C@H]2COc3c(Cl)cc(S(C)(=O)=O)cc3O2)cc1
[(2R)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate
CCN
ethanamine
—
amine

Reagenzien

Keine

Lösungsmittel

CC#N
ACN

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePreparation
  2. 2
    Sonstigecrystallized from MeOH/Et2O
  3. 3
    Sonstige[α]=−62° (MeOH)

Vorschrift

Preparation according to Example 5 using [(2R)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.47 g, 1.09 mmol), ethanamine (1 ml, 70% in water) and ACN (7 ml). Yield: 0.278 g, 83%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 267° C. MS m/z (rel. intensity, 70 eV) 305 (M+, 4), 63 (3), 59 (4), 58 (bp), 56 (5). [α]=−62° (MeOH).

Quelle

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