P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:7][C:8]([CH3:20])([O:10][CH2:11][CH:12](O)[CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH3:9].[ClH:21]>C1(C)C=CC=CC=1.O1CCCC1>[Cl:21][CH:12]([CH2:11][O:10][C:8]([CH3:20])([CH3:9])[CH3:7])[CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1To a stirred, cooled suspension of 34.7 g (0.167 ml) of phosphorous pentachloride in 20 ml of dry toluene (argon atmosphere) was added a solution of 31.93 g (0.159 m) of 1-[3-(1,1-dimethylethoxy)-2-hydroxypropyl]pyrrolidine (the product of Example 13a) and excess hydrogen chloride (gas) in 46 ml of dry toluene and 50 ml of dry tetrahydrofuran at a rate to keep the reaction temperature at 10°-25° C. When the addition was completed, the cooling bath was removed and the reaction mixture was stirred at ambient temperature for 1.5 hr. The reaction mixture was added portionwise, with stirring to a cooled solution of 122 ml of 45% potassium hydroxide and 230 g of ice at a rate to keep the reaction temperature at 25°-35° C. The reaction mixture was partitioned between ether and water. The ether portion was dried and concentrated in vacuo to give 31.69 g of oily title compound.
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