[CH2:1]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(C(OCC)=O)=NC(OCC)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CCOCC>[CH2:1]([N:8]1[CH:14]2[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Cyclization of 2-Benzylamino-cyclohexanol. Diethyl azodicarboxylate (Aldrich, 95%, 3.6 ml, 22.6 mmol) was slowly added to an ether solution (50 ml) of 2-benzylaminio-cyclohexanol (3.1 g, 15 mmol) and PPh3 (5.94 g, 22.6 mmol) under N2, with stirring, in an ice-bath. After addition, the ice bath was removed, and the mixture stirred at room temperature for 36 h. The resulting crystalline precipitate was filtered and the solvent removed from the filtrate by rotary evaporation to yield the crude product, which was purified by column chromatography (petroleum ether: diethyl ether=50:50) (2.1 g, 75% yield).
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