O[CH:2]([C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[O:28][C@@H:27]([CH3:34])[CH2:26]2)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][C:5]1([CH2:21][OH:22])[CH3:20].C(C=P(CCCC)(CCCC)CCCC)#N>C1C=CC=CC=1>[CH3:20][C:5]12[CH2:6][N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:8][CH2:9][N:4]1[CH2:3][CH:2]([C:23]1[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[O:28][C@@H:27]([CH3:34])[CH2:26]3)[O:22][CH2:21]2The mixture of benzyl 4-(2-hydroxy-2-((S)-3-methyl-1-oxoisochroman-6-yl)ethyl)-3-(hydroxymethyl)-3-methylpiperazine-1-carboxylate (762 mg, 1.60 mmol) and cyanomethylenetributylphosphorane (471 mg, 1.90 mmol) in dry benzene was degassed and heated to 135° C. in a microwave reactor for 3.5 h. After which point, the reaction mixture was cooled down to rt, concentrated to dryness and purified on silica gel to afford the title compound (cis or trans): MS: m/e 451.2 (M+H)+.
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