Triethylamine → (1-(Cyanomethyl)cyclopropyl)methyl Methanesulfonate
Reaktionsgleichung
[OH:1][CH2:2][C:3]1([CH2:6][C:7]#[N:8])[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:16][S:17]([O:1][CH2:2][C:3]1([CH2:6][C:7]#[N:8])[CH2:5][CH2:4]1)(=[O:19])=[O:18]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -10 °C
Versuchsvorschrift
To a solution of [1-(hydroxymethyl)cyclopropyl]acetonitrile (prepared according to the procedure described in WO2005/105749 Example 2/Step 4) (1 eq.) in DCM at −40° C. was added triethylamine (3 eq.) and then methanesulfonyl chloride (1.5 eq.). The reaction was warmed to −10° C. over 1 h, and it was diluted with DCM and quenched with saturated aqueous NaHCO3. The aqueous phase was extracted with DCM. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 0%→50% EtOAc in Hex) to afford the title compound appendage 4 as an oil.
Aufarbeitung
- customat −40° C.
- customquenched with saturated aqueous NaHCO3
- extractionThe aqueous phase was extracted with DCM
- dry with materialThe combined organic extracts were dried over MgSO4
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash column chromatography (SiO2, 0%→50% EtOAc in Hex)
Quellen und Nachweise
- ORD-Eintrag
- ord-8ca2ff93baa44874840069d90ea047b9
- Quelldatensatz
- uspto-grants-2013_01
- Patentnummer
- US08343968B2
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