反应详情

To a solution of (2S,4S)-4-acetylthio-2-hydroxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (15 g) in a mixture of methanol (150 ml) and tetrahydrofuran (150 ml) was added a 28% solution of sodium methoxide in methanol (8.95 ml) under ice-cooling and the mixture was stirred at the same temperature for 10 minutes. To the mixture was added triphenylmethyl chloride (12.39 g) on ice bath, followed by stirring at the same temperature for 1 hour. The precipitates were filtered off and the filtrate was evaporated in vacuo to give a residue. The residue was dissolved in ethyl acetate (200 ml), washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was chromatographed on silica gel (200 g) eluting with a mixture of dichloromethane and acetone (9:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-2-hydroxymethyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (22.24 g).

1. temperaturecooling
2. stirringby stirring at the same temperature for 1 hour
3. filtrationThe precipitates were filtered off
4. customthe filtrate was evaporated in vacuo
5. customto give a residue
6. washwashed with water
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customto give a syrup
10. customThe syrup was chromatographed on silica gel (200 g)
11. washeluting with a mixture of dichloromethane and acetone (9:1 V/V)
12. additionThe fractions containing the desired compound
13. customwere collected
14. customevaporated in vacuo