Diisopropylethylamine → rac-{(3S,4R)-4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-ethyl-carbamic acid 4-fluoro-phenyl ester

HRID 527474

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:13]([NH:14][CH2:15][CH3:16])[CH2:12][N:11]([C:17]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([C:27]4([CH3:30])[CH2:29][CH2:28]4)=[O:26])[CH2:21][CH2:20]3)=[O:18])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)C(C)C)(C)C.Cl[C:41]([O:43][C:44]1[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=1)=[O:42]>ClCCl>[F:50][C:47]1[CH:48]=[CH:49][C:44]([O:43][C:41](=[O:42])[N:14]([C@H:13]2[C@H:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH2:10][N:11]([C:17]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([C:27]4([CH3:30])[CH2:29][CH2:28]4)=[O:26])[CH2:21][CH2:20]3)=[O:18])[CH2:12]2)[CH2:15][CH3:16])=[CH:45][CH:46]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of rac-[(3R,4S)-3-(3,4-dichloro-phenyl)-4-ethylamino-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone (25 mg, 0.06 mmol) in dichloromethane (1 mL) was added N,N-diisopropylethylamine (10 uL, 0.06 mmol). It was cooled to 0° C. and 4-fluorophenyl chloroformate (8 uL, 0.06 mmol) was added and the reaction mixture was stirred for 30 min at this temperature and then 2 h at ambient temperature. Concentration and purification by chromatography (SiO2, ethyl acetate) afforded the title compound (17 mg, 52%) as a colorless foam. MS m/e: 590.4 [M]+.

Aufarbeitung

custom2 h
customat ambient temperature
concentrationConcentration and purification by chromatography (SiO2, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-2042bf509cd843bda3094c6e797f0501
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09346786B2

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