(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonate → HCID 10299703, Verbindung

HRID 982626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 982626
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:27][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14]2)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]4)(=O)=O)=CC=1.[F:28][C:29]([F:46])([F:45])[C:30]1[CH:31]=[C:32]([C:36]2([OH:44])[CH2:42][CH:41]3[NH:43][CH:38]([CH2:39][CH2:40]3)[CH2:37]2)[CH:33]=[CH:34][CH:35]=1>CS(C)=O>[CH3:26][C:21]1[CH:20]=[CH:19][C:18]2[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14][CH:13]([CH2:12][N:43]4[CH:41]5[CH2:40][CH2:39][CH:38]4[CH2:37][C:36]([C:32]4[CH:33]=[CH:34][CH:35]=[C:30]([C:29]([F:28])([F:45])[F:46])[CH:31]=4)([OH:44])[CH2:42]5)[O:27][C:17]3=2)[N:22]=1

Komponenten

4

Edukt 2

HCID 11280604(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonateHCID 13091256HCID 13091256, Verbindung

Produkt 1

HCID 10299703HCID 10299703, VerbindungAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(2R)-8-Methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonate (0.70 g, 1.8 mmole) and 3-(3-trifluoromethyl-phenyl)-8-azabicyclo[3.2.1]octan-3-ol (0.59 g, 2.4 mmole) were combined in 3 mL of DMSO and heated at 100° C. under nitrogen for 4 hours. After cooling to room temperature, the mixture was partitioned between 400 mL of ethyl acetate and 400 mL of saturated sodium bicarbonate solution. The organic phase was removed, washed with 400 mL of water, dried over magnesium sulfate, filtered and concentrated in vacuum to 1.29 g of a crude oil. The residue was column chromatographed on silica gel using 10% methanol in ethyl acetate as eluant to give 0.30 g of a yellow oil. Crystallization from ethanol/ether with the addition of 0.073 g of fumaric acid gave 0 040 g of the (S)-enantiomer of the title compound as a light yellow solid, m.p. 146-150° C.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between 400 mL of ethyl acetate and 400 mL of saturated sodium bicarbonate solution
  3. customThe organic phase was removed
  4. washwashed with 400 mL of water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum to 1.29 g of a crude oil
  8. customchromatographed on silica gel using 10% methanol in ethyl acetate as eluant

Quellen und Nachweise

ORD-Eintrag
ord-1055bc87414f484e8f6ba1f7676d53b8
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06861427B2

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