Water → HCID 21706365, compound

Participants

Reaction Steps

5-[4-[3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophen-2-yl]phenoxy]pentanoic acid ethyl ester prepared in part A (78 mg; 0.14 mmol) was dissolved in 3 mL of anhydrous THF under an argon atmosphere, then LAH (10 mg; 0.29 mmol) was added. The resultant mixture was stirred at room temperature for 3 h. To the reaction was added 1 drop of water, 1 drop of 5 M NaOH, and 3 drops of water. The mixture was stirred at room temperature for 45 min, then water (25 mL) was added. Extraction was carried out with EtOAc (4×25 mL). The combined organics were dried by passage through Na2SO4. The product was isolated as a colorless oil (49 mg; 66%) by flash chromatography on silica gel, eluting with EtOAc(10-90%)/Et3N(0-5%)/MeOH(0-5%). Conversion to the oxalate was effected in the usual way.

Provenance & Evidence