Reaktion #67237

ord-98c92b8795d844bdb3ba044769f2da92

Reaktionsgleichung

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
CN
methanamine
→
CNC[C@H]1COc2c(Cl)cc(S(C)(=O)=O)cc2O1
title compound
Ausbeute 56.1%
CNC[C@H]1COc2c(Cl)cc(S(C)(=O)=O)cc2O1
1-[(2S)-5-CHLORO-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]-N-METHYLMETHANAMINE
Ausbeute 56.1%

Edukte

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
CN
methanamine

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)

Vorschrift

A mixture of [(2R)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.48 g, 1.1 mmol), methanamine (1.5 ml, 33% in EtOH, 4 mmol) and ACN (3 ml) was heated under microwave radiation at 120° C. for 20 min. Purification on SCX-3 column (TEA/MeOH) and by flash column chromatography (MeOH/EtOAc) gave the title compound (0.18 g). The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 262° C. MS m/z (rel. intensity, 70 eV) 291 (M+, 43), 113 (57), 85 (80), 70 (bp), 63 (84), 50 (60) [α]=−61° (MeOH).

Quelle

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