C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[Cl:21])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O.CO>C(Cl)Cl>[Cl:21][CH:15]1[CH:14]([CH:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH:19]=[CH:18][C:17]([F:20])=[CH:16]1Dissolve 4-benzyl-2-(2-chloro-4-fluoro-phenyl)morpholine (529 mg, 1.73 mmol) in DCM (2.5 mL). Add 1-chloroethyl chloroformate (1.25 g, 8.65 mmol); heat to 80° C.; and stir overnight. Add MeOH (2.5 mL) and stir at 65° C. for 3 hours. Concentrate under reduced pressure and purify via SCX chromatography eluting with a gradient of 0-100% of (2N NH3/MeOH) in MeOH. Combine the product fractions and remove the solvents under reduced pressure to provide the title compound as a white solid (345 mg, 92%). MS (m/z): 216 (M+1).
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