[OH:1][C:2]1[C:11]2[CH:10]3[CH:12]=[C:13]([CH3:16])[CH2:14][CH2:15][CH:9]3[C:8]([CH3:18])([CH3:17])[O:7][C:6]=2[CH:5]=[C:4]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:3]=1.Cl.[N:25]1([CH2:31][CH2:32][CH2:33][C:34](O)=[O:35])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C1(N=C=NC2CCCCC2)CCCCC1.C(Cl)[Cl:53]>CO.C(Cl)(Cl)Cl>[ClH:53].[CH2:19]([C:4]1[CH:3]=[C:2]([O:1][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:11]2[CH:10]3[CH:12]=[C:13]([CH3:16])[CH2:14][CH2:15][CH:9]3[C:8]([CH3:17])([CH3:18])[O:7][C:6]=2[CH:5]=1)[CH2:20][CH2:21][CH2:22][CH3:23]0.46 g. (1.47 mmoles) of 1-Hydroxy-3-n-pentyl-6,6,9-trimethyl-10a,6a,7,8 -tetrahydrodibenzo[b,d]pyran, 0.31 g. (1.47 mmoles) of γ-piperidinobutyric acid hydrochloride and 0.32 g. (1.55 mmoles) of dicyclohexylcarbodiimide were combined in 25 ml. of methylene chloride and stirred at room temperature for 4 hours. The insoluble by-product of dicyclohexylurea was removed by filtration and the methylene chloride was evaporated to give a gummy yellowish residue. The gummy material was triturated several times with petroleum ether and dried in vacuo to give 350 mg. of product as a colorless foam-like solid. The sample was pure by thin-layer chromatography (10% MeOH/CHCl3) and the infrared spectrum was consistent with the proposed structure.
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