Water → 4-[4-[6-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophen-2-yl]phenoxy]butanol Oxalate

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The 4-[4-[6-benzyloxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophen-2-yl]phenoxy]butanoic acid methyl ester prepared in Part A (91 mg; 0.14 mmol) was dissolved in anhydrous THF under argon atmosphere. LAH (10 mg; 0.29 mmol) was added. The mixture was stirred at room temperature for 3 h before it was hydrolyzed by addition of 2 drops of water, 2 drops of 5 M NaOH, and six drops of water. Additional water (25 mL) was added, and extraction was carried out with CH2Cl2. The combined organics were dried by passage through Na2SO4. Purification was effected by flash chromatography on silica gel, eluting with EtOAc(100-90%)/Et3N(0-5%)/MeOH(0-5%). The title product was obtained as a colorless oil (74 mg, 85%).

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