反应详情

Benzyl (S)-1-((1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-isopropylcyclohexylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate (5.3 g) was dissolved in iodomethane (90 mL), and the resulting solution was stirred at rt for 72 h before being concentrated in vacuo. The residue was dissolved in methylene chloride, and the resulting solution was concentrated; this was repeated to afford the salt. MS found: (M+H)+=586.5. This material was dissolved in DMSO (30 mL) and the solution was charged with Cs2CO3 (12.7 g). After 6 h, the reaction was partitioned between EtOAc and brine. The organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography to afford benzyl (S)-1-((1S,2S,4R)-4-hydroxy-2-isopropylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate [580 mg; MS found: (M+H)+=375.3] and benzyl (S)-1-((1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-isopropylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate [1.0 g; MS found: (M+H)+=489.4].

1. concentrationbefore being concentrated in vacuo
2. dissolutionThe residue was dissolved in methylene chloride
3. concentrationthe resulting solution was concentrated
4. customto afford the salt
5. waitAfter 6 h
6. customthe reaction was partitioned between EtOAc and brine
7. dry with materialThe organic phase was dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified by flash chromatography