Ethanol → 3-(4-Propoxy-1H-pyrazol-3-yl)-1-azabicyclo[2.2.2]octane

HRID 660178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660178
[CH2:1]([OH:4])[CH2:2][CH3:3].I[C:6]1[C:7]([CH:19]2[CH:24]3[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]3)[CH2:20]2)=[N:8][N:9](COCC[Si](C)(C)C)[CH:10]=1.CCO.CCO.C(N(CC)CC)C>CCO.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:1]([O:4][C:6]1[C:7]([CH:19]2[CH:24]3[CH2:23][CH2:22][N:21]([CH2:26][CH2:25]3)[CH2:20]2)=[N:8][NH:9][CH:10]=1)[CH2:2][CH3:3]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 10311-PropanolHCID 22663003EtOH triethylamineHCID 575480683-[4-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-1-azabicyclo[2.2.2]octane

Produkt 1

HCID 1784588093-(4-Propoxy-1H-pyrazol-3-yl)-1-azabicyclo[2.2.2]octane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22328969EtOH ethyl acetate triethylamineLösungsmittel

Versuchsvorschrift

Compound 52B was prepared following the procedure as described for the synthesis of compound 52A (see Scheme 10) using propanol and 3-[4-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-1-azabicyclo[2.2.2]octane (50). Work-up and flash chromatography (gradient EtOH to EtOH/triethylamine 300/1) followed by a second flash chromatography (EtOH/ethyl acetate/triethylamine 25/75/1) afforded compound 51B as an oil (14%). LCMS (method B): Rt: 7.15 min, ([M+H]+=366). Compound 51A was subsequently deprotected (TBAF/THF) and purified by flash chromatography (gradient EtOH to EtOH/triethylamine 97/3), followed by a preparative TLC purification (CH3CN/H2O) to afford the title compound 52B as an oil. (51%). LCMS (method A); Rt: 0.91 min, ([M+H]+=236). 1H-NMR (600 MHz, D6DMSO): δ 7.34 (s, 1H), 3.74 (t, J=7 Hz, 2H), 3.24-3.19 (m, 1H), 3.03-2.96 (m, 1H), 2.92-2.87 (m, 1H), 2.86-2.74 (m, 3H), 2.69-2.62 (m, 1H), 1.88-1.84 (m, 1H), 1.67-1.55 (m, 5H), 1.26-1.20 (m, 1H), 0.92 (t, J=7 Hz, 3H).

Quellen und Nachweise

ORD-Eintrag
ord-2679bc12793742edba84ad81af6fbec8
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084473B2

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