tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylate → tert-Butyl (2S)-2-methylpyrrolidine-1-carboxylate

To a solution of 2-(S)-(toluene-4-sulfonyloxymethyl)-pyrrolidine- 1-carboxylic acid tert-butyl ester (compound (4), 1.77 g, 4.99 mmol) in 5 mL of THF at 0° C. was added dropwise 15 mL (15 mmol) of a 1 M THF solution of lithium triethylborohydride. After 15 hours, the reaction was quenched by addition of 7.39 mL of water. The reaction was diluted with 35 mL of chloroform, and poured into a separatory funnel. The mixture was diluted with dichloromethane and washed with saturated aqueous NaCl solution. The organic phase then was dried over sodium sulfate. The mixture was concentrated in vacuo and purified by flash chromatography on silica gel, eluting with 1:3 ethyl acetate/hexane to give pure product as a clear oil (0.73 g, 79% yield).

1. customthe reaction was quenched by addition of 7.39 mL of water
2. additionThe reaction was diluted with 35 mL of chloroform
3. additionpoured into a separatory funnel
4. additionThe mixture was diluted with dichloromethane
5. washwashed with saturated aqueous NaCl solution
6. dry with materialThe organic phase then was dried over sodium sulfate
7. concentrationThe mixture was concentrated in vacuo
8. custompurified by flash chromatography on silica gel
9. washeluting with 1:3 ethyl acetate/hexane

ORD record

ord-c85ec483d9e54f9e962711ba6b07617a

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07244852B2