反应详情

To a solution of 13.1 mL (26.25 mmol) of oxalyl chloride (2M in DCM) in 13 mL of anhydrous DCM were added 3.72 mL (52.5 mmol) of DMSO at −78° C. After 5 minutes of stirring, 3 g (10.5 mmol) of 3-(RS)-hydroxymethyl-4-(SR)-phenylpyrrolidine-1-carboxylic acid tert-butyl ester, previously dissolved in 15 mL of anhydrous DCM, were added dropwise. After 30 minutes additional agitation at −78° C., 18.5 mL (105 mmol) of DIPEA were added dropwise. An additional 30 minutes of agitation at 0° C. and the reaction mixture was quenched with 10 mL of water. 100 mL of water were again added and the solution was extracted with DCM (2×100 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated in vacuo. The crude yellow oil was purified by flash chromatography on silica gel (ethyl acetate/hexanes 0:100 to 20:80) yielding 2.42 g (83.7%) of 3-(RS)-formyl-4-(SR)-phenylpyrrolidine-1-carboxylic acid tert-butyl ester as a pale yellow oil.

1. additionwere added dropwise
2. waitAfter 30 minutes additional agitation at −78° C.
3. customAn additional 30 minutes of agitation at 0° C. and the reaction mixture was quenched with 10 mL of water
4. addition100 mL of water were again added
5. extractionthe solution was extracted with DCM (2×100 mL)
6. dry with materialThe combined organic layers were dried over sodium sulfate
7. filtrationfiltered
8. customevaporated in vacuo
9. customThe crude yellow oil was purified by flash chromatography on silica gel (ethyl acetate/hexanes 0:100 to 20:80)