Reaktion #67180

ord-d84aadf79e9d4b37a7fc8f1cc9cf6258

Reaktionsgleichung

Cl
hydrochloric acid
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
CN
methanamine
→
CNC[C@H]1COc2ccc(S(C)(=O)=O)cc2O1
N-METHYL-1-[(2S)-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHANAMINE

Edukte

Cl
hydrochloric acid
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
CN
methanamine
—
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]=−59° (MeOH)

Vorschrift

Preparation according to Example 3 using [(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.4 g, 1 mmol), methanamine (33% in EtOH, 1 ml) and ACN (3 ml). Yield: 0.2 g, 89%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 248° C. MS m/z (rel. intensity, 70 eV) 257 (M+, bp), 79 (86), 70 (59), 63 (50), 51 (71). [α]=−59° (MeOH).

Quelle

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