Reaktion #67177

ord-16b71b8e120d4bb6982c7b1a6a606d22

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
C1CCNCC1
piperidine
→
CS(=O)(=O)c1ccc2c(c1)O[C@@H](CN1CCCCC1)CO2
1-{[(2S)-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL}PIPERIDINE

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
C1CCNCC1
piperidine
—
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]=−65° (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), piperidine (1 ml) and ACN (3 ml). Yield: 0.3 g, 94%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 227° C. MS m/z (rel. intensity, 70 eV) 311 (M+, 1), 310 (M+, 1), 99 (7), 98 (bp), 79 (2), 55 (4). [α]=−65° (MeOH).

Quelle

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