反应详情

To a solution of (2S,3R)-3-(tert-Butyldimethylsilanyloxy)-2-methylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester-2-methyl ester (58A) (1.08 g, 2.90 mmol) in THF (12 mL) at −78° C. was added a 1 M solution of Super-Hydride® in THF (14.50 mL, 14.50 mmol) in three portions over 15 min. After 10 min, the cold bath was removed and the reaction was allowed to warm to rt and was stirred for 18 h. The reaction was cooled again to −78° C. and more Super-Hydride® (7 mL) was added. After stirring an additional 24 h, the reaction was poured into a 1-L Erlenmeyer flask containing ice water and was then diluted with EtOAc. The layers were separated and the organic layer washed with 1 M H3PO4 (2×), NaHCO3 and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was diluted with CH2Cl2, stirred with silica gel for 10 min, then concentrated under reduced pressure and purified via flash chromatography, eluting with 20% EtOAc/hexane to obtain the title compound (0.54 g) as a clear oil. MS m/z 346 [M+H]+.

1. customthe cold bath was removed
2. temperatureThe reaction was cooled again to −78° C.
3. additionmore Super-Hydride® (7 mL) was added
4. stirringAfter stirring an additional 24 h
5. additionthe reaction was poured into a 1-L Erlenmeyer flask
6. additioncontaining ice water
7. additionwas then diluted with EtOAc
8. customThe layers were separated
9. washthe organic layer washed with 1 M H3PO4 (2×), NaHCO3 and brine
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. additionThe residue was diluted with CH2Cl2
14. stirringstirred with silica gel for 10 min
15. concentrationconcentrated under reduced pressure
16. custompurified via flash chromatography
17. washeluting with 20% EtOAc/hexane