Piperazine → (2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-(piperazin-1-yl)methyl-4-(triphenylmethylthio)pyrrolidine

To a solution of (2S,4S)-2-(methanesulfonyloxy)-methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (5.0 g) in dimethylformamide (90 ml) was added piperazine (2.0 g) and the mixture was stirred at 80°]90°C. for 5 hours. The reaction mixture was poured into ice-water (300 ml) and extracted twice with ethyl acetate (200 ml). The extract was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (150 g) eluting with a mixture of chloroform and methanol (9:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-(piperazin-1-yl)methyl-4-(triphenylmethylthio)pyrrolidine (2.52 g).

1. extractionextracted twice with ethyl acetate (200 ml)
2. washThe extract was washed with saturated aqueous sodium chloride
3. dry with materialdried over magnesium sulfate
4. customevaporated in vacuo
5. customThe resulting residue was chromatographed on silica gel (150 g)
6. washeluting with a mixture of chloroform and methanol (9:1 V/V)
7. additionThe fractions containing the desired compound
8. customwere collected
9. customevaporated in vacuo

ORD 기록

ord-a5b068a6087b4855b8be83c1e7c63d9f

출처 데이터셋

uspto-grants-1993_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05202437