Pyridine → Methanesulfonic acid 2-[4-(piperidine-1-carbonyl)-1,2,3,4-tetrahydro-carbazol-9-yl]-ethyl ester

HRID 1753930Notizen

Reaktionsgleichung

[OH:1][CH2:2][CH2:3][N:4]1[C:16]2[CH2:15][CH2:14][CH2:13][CH:12]([C:17]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])[C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.N1C=CC=CC=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[N:19]1([C:17]([CH:12]2[C:11]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[N:4]([CH2:3][CH2:2][O:1][S:32]([CH3:31])(=[O:34])=[O:33])[C:16]=3[CH2:15][CH2:14][CH2:13]2)=[O:18])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of [9-(2-hydroxy-ethyl)-2,3,4,9-tetrahydro-1H-carbazol-4-yl]-piperidin-1-yl-methanone (23) (260 mg, 0.8 mmol) in dichloromethane (15 mL) was added pyridine (633 mg, 8.0 mmol, 0.65 mL). The reaction was cooled to 0° C. and methanesulfonyl chloride (458 mg, 4.0 mmol, 0.31 mL) was added. The reaction was allowed to warm to room temperature overnight. The mixture was washed with 2 N HCl (2×50 mL) and water (2×50 mL), dried and concentrated in vacuo. The crude material was triturated with diethyl ether to afford 263 mg (82%) of methanesulfonic acid 2-[4-(piperidine-1-carbonyl)-1,2,3,4-tetrahydro-carbazol-9-yl]-ethyl ester as a white solid. The structure was confirmed by 13C NMR (75 MHz, CDCl3) δC 21.4, 21.8, 24.7, 25.9, 26.9, 27.4, 36.6, 36.8, 41.7, 43.3, 47.0, 67.9, 108.5, 109.5, 118.4, 119.7, 121.3, 126.9, 136.2, 172.7.

Aufarbeitung

temperatureto warm to room temperature overnight
washThe mixture was washed with 2 N HCl (2×50 mL) and water (2×50 mL)
customdried
concentrationconcentrated in vacuo
customThe crude material was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag: ord-fd334cc17bbb40f99f4eb008f9804b3a
Quelldatensatz: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09168317B2

Notizen zur Reaktion

Wird geladen…