反应详情

1-Phenyl-1H-tetrazole-5-thiol (9.0 g) and triphenylphosphine (13.2 g) were added to a solution of (R)-(−)-5-(hydroxymethyl)-2-pyrrolidinone (4.5 g) in tetrahydrofuran (90 mL), followed by ice-cooling. A solution of 2.2 M diethyl azodicarboxylate in toluene (23 mL) was added dropwise thereto, and the mixture was stirred at room temperature overnight. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=4:1→1:1→0:1) to give (R)-5-{[(1-phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}pyrrolidin-2-one (1.98 g) as a colorless oil.

1. temperaturecooling
2. extractionfollowed by extraction with ethyl acetate
3. washThe organic layer was washed with brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. customThe solvent was then evaporated under reduced pressure
7. customThe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=4:1→1:1→0:1)