C[N:2]1[CH:7]2[CH2:8][C:9]([CH2:11][CH:3]1[CH2:4][CH2:5][CH2:6]2)=[O:10].[Cl:12][C:13]([Cl:20])([Cl:19])[CH2:14][O:15][C:16](Cl)=[O:17].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.Cl.C(=O)([O-])[O-].[K+].[K+]>[Cl:12][C:13]([Cl:20])([Cl:19])[CH2:14][O:15][C:16]([N:2]1[CH:7]2[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:11][C:9](=[O:10])[CH2:8]2)=[O:17]
To a solution of pseudopelletierine (52 g, 0.34 mol) in toluene (220 mL) at 50° C. was added anhydrous potassium carbonate (1.0 g), followed by the slow addition of trichloroethylchloroformate (79 g, 0.37 mol). After addition was completed (30 minutes), triethylamine (10 mL) was added. The reaction was allowed to cool to room temperature and stirred for 18 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and 1N hydrochloric acid (200 mL). After the organic layer was washed with 1N hydrochloric acid (100 mL), it was washed with aqueous 10% sodium hydroxide (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford a beige solid which was triturated with hexane (300 mL) to afford 81.4 g of crystalline solid (76% yield); mp 95°-96° C. after recrystallization from ethyl acetate-hexane. Anal. (C11H14C13NO3).
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