(8R)-2-Methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-ylmethyl 4-methylbenzenesulfonate → N-[(trans)-3-(5-Fluoro-1H-indol-3-yl)cyclopentyl]-N-{[(8S)-2-methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-yl]methyl}amine

HRID 1072457

Reaktionsgleichung

Reaktionsgleichung von HRID 1072457
[CH3:1][C:2]1[O:26][C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[N:3]=1)[O:10][CH2:9][C@H:8]([CH2:14]OS(C1C=CC(C)=CC=1)(=O)=O)[O:7]3.[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][CH:32]=[C:31]2[CH:37]1[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38]1>CS(C)=O>[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][CH:32]=[C:31]2[C@H:37]1[CH2:41][CH2:40][C@H:39]([NH:42][CH2:14][C@H:8]2[CH2:9][O:10][C:11]3[CH:12]=[CH:13][C:4]4[N:3]=[C:2]([CH3:1])[O:26][C:5]=4[C:6]=3[O:7]2)[CH2:38]1

Komponenten

4

Edukt 2

HCID 11245807(8R)-2-Methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-ylmethyl 4-methylbenzenesulfonateHCID 221491433-(5-fluoro-1H-indol-3-yl)-cyclopentylamine

Produkt 1

HCID 69564251N-[(trans)-3-(5-Fluoro-1H-indol-3-yl)cyclopentyl]-N-{[(8S)-2-methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-yl]methyl}amineAusbeute 34,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
77.5 °C

Versuchsvorschrift

Toluene-4-sulfonic acid (8R)-2-methyl-7,8-dihydro-1,6,9-trioxa-3-aza-cyclo-penta[a]naphthlen-8-ylmethyl ester (0.46 g, 1.2 mmole) and 3-(5-fluoro-1H-indol-3-yl)-cyclopentylamine (0.27 g, 1.2 mmole) were combined in 8 mL of DMSO under nitrogen. This solution was heated to 75-80° C. under nitrogen for 5 hours. After cooling to room temperature, the reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuo. Flash chromatography on silica gel (CH2Cl2 then 1% MeOH/CH2Cl2) afforded 0.175 g of the title compound as an off-white solid: m.p. 79-82° C.; MS (ESI) m/z 422 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-85b78c23cf9f447caa4ad8064d008cc1
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911445B2

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