1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Vinyl-morpholine-2,4-dicarboxylic acid 4-tert-butyl ester 2-methyl ester
Reaktionsgleichung
[CH3:1][O:2][C:3]([C:5]1([CH:18](OS(C(F)(F)F)(=O)=O)[CH3:19])[O:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)=[O:4].N12CCCN=C1CCCCC2>ClCCl>[CH3:1][O:2][C:3]([C:5]1([CH:18]=[CH2:19])[O:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH2:6]1)=[O:4]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 35 °C
Versuchsvorschrift
A warm (35° C.) solution of 2-(1-trifluoromethanesulfonyloxy-ethyl)-morpholine-2,4-dicarboxylic acid 4-tert-butyl ester 2-methyl ester (1.384 g, 3.284 mmol) in dichloromethane (40 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (2.5 mL, 16.422 mmol). After stirring at 35° C. for 2 h, the reaction was cooled to 0° C. and quenched with hydrochloric acid (1 M, 50 mL). The aqueous layer was extracted with dichloromethane. The organics were combined, filtered through a phase separator and the volatiles were removed in vacuo to provide the title compound as an orange oil which was used without further purification in the next step. 1H NMR (300 MHz, CDCl3) δ 1.49 (s, 9H), 3.13-3.29 (m, 2H), 3.60-3.73 (m, 1H), 3.79 (s, 3H), 3.83-3.92 (m, 2H), 4.24 (d, J=13.1 Hz, 1H), 5.37 (d, J=10.9 Hz, 1H), 5.55 (d, J=17.4 Hz, 1H), 5.84 (dd, J=17.4, 10.9 Hz, 1H).
Aufarbeitung
- temperaturethe reaction was cooled to 0° C.
- customquenched with hydrochloric acid (1 M, 50 mL)
- extractionThe aqueous layer was extracted with dichloromethane
- filtrationfiltered through a phase separator
- customthe volatiles were removed in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-3250a752892644fa9120e88b66c1270c
- Quelldatensatz
- uspto-grants-2015_06
- Patentnummer
- US09062092B2
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