Reaktion #67182

ord-b456ce4360a84ba2ac3b3cb60427655f

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
CC1CCCNC1
3-methylpiperidine
→
CC1CCCN(C[C@@H]2COc3ccc(S(C)(=O)=O)cc3O2)C1
3-METHYL-1-{[(2R)-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL}PIPERIDINE

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
CC1CCCNC1
3-methylpiperidine

Reagenzien

Keine

Lösungsmittel

CC#N
ACN

Reaktionsbedingungen

Temperatur
120°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePurification on flash column chromatography (Isooctane/EtOAc/MeOH)
  2. 2
    Sonstigecrystallized from MeOH/(i-Pr)2O
  3. 3
    Sonstige[α]=+50° (MeOH)

Vorschrift

A mixture of [(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.20 g, 0.5 mmol), 3-methylpiperidine (0.35 ml, 3 mmol) and ACN (2 ml) was heated under microwave radiation at 120° C. for 30 min. Purification on flash column chromatography (Isooctane/EtOAc/MeOH). Yield: 0.097 g, 85%. The amine was converted to the fumaric acid salt and crystallized from MeOH/(i-Pr)2O. M.p. 159° C. MS m/z (rel. intensity, 70 eV) 325 (M+, 1), 113 (83), 112 (bp), 69 (43), 55 (46). [α]=+50° (MeOH).

Quelle

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