4-Methylmorpholine → Allyl 1-{[(alpha-Chloroethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

HRID 30516

Reaktionsgleichung

Cl.[NH2:2][CH2:3][C:4]1([CH2:10][C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.Cl[C:18]([O:20][CH:21]([Cl:23])[CH3:22])=[O:19].CN1CCOCC1>ClCCl.C(OCC)C>[Cl:23][CH:21]([O:20][C:18]([NH:2][CH2:3][C:4]1([CH2:10][C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[O:19])[CH3:22]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of compound (13) (30 g, 0.121 mol) in dichloromethane (100 mL) was slowly added 1-chloroethyl chloroformate (13 mL, 16.9 g, 0.119 mol). The reaction mixture was cooled to 0° C. and N-methylmorpholine (26.39 mL, 24.28 g, 0.24 mol) was slowly added over a period of 1 h while maintaining a temperature of less than 10° C. The resulting turbid solution was stirred for 30 min, and the reaction mixture was then diluted with diethyl ether (250 mL), washed with water (100 mL) and brine (100 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated to give the desired product (14) as light yellow viscous liquid (38 g, 99% yield). 1H NMR (CDCl3, 400 MHz): δ 1.35-1.58 (m, 10H), 1.78 (d, 3H), 2.32 (s, 2H), 3.22 (d, 2H), 4.57 (d, 2H), 5.25 (dd, 1H), 5.32 (dd, 1H), 5.52 (br. s, 1H), 5.90-5.94 (m, 1H), 6.54 (q, 1H).

Aufarbeitung

temperaturewhile maintaining a temperature of less than 10° C
washwashed with water (100 mL) and brine (100 mL)
dry with materialThe organic phase was dried over anhydrous sodium sulfate
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-a915ccb62cee4ba8b6552be00937a3f4
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07423169B2

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