Tetracyanoquinodimethane → HCID 58580848, compound

Participants

Reaction Steps

A solution of ethyl (2E)-3-{2-[(1R)-1-({(2R)-3-[(2S)-2-(4-chloro-3-fluorobenzyl)pyrrolidin-1-yl]-2-hydroxypropyl}oxy)ethyl]-6-methoxy phenyl}prop-2-enoate (516 mg, 992.3 μmol), which had been obtained in Example 168 (168a), in mixture of tetrahydrofuran (10 mL) and ethanol (2 mL) was added with nickel (II) chloride hexahydrate (117.9 mg, 496.1 μmol) and 7,7,8,8-tetracyanoquinodimethane (101.3 mg, 496.1 μmol), and stirred for 5 minutes under ice cooling. After stirring, a solution of sodium borohydride (150 mg, 3.97 mmol) in mixture of tetrahydrofuran (5 mL) and ethanol (1 mL) was added dropwise slowly thereto under ice cooling. Upon the completion of the dropwise addition, the mixture was stirred for 1 hour at room temperature, added with water (20 mL), and filtered. The solvent was distilled off under reduced pressure. The residue was extracted with ethyl acetate (40 mL×2). After that, the organic layers were washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=1/2) to give the title compound as a colorless oily substance (253 mg, yield 49%).

Provenance & Evidence