Potassium Bromide → (S)-tert-butyl 3-formylpyrrolidine-1-carboxylate

Temperature

-4 °C

To a solution of (S)-3-hydroxymethyl-pyrrolidine-1-carboxylic acid t-butyl ester (4.0 g, 19.9 mmol, 1.0 eq.) in DCM was added TEMPO (62 mg, 0.4 mmol, 0.02 eq.) and potassium bromide (120 mg, 1.0 mmol, 0.05 eq.). The resulting mixture was cooled over ice (and a small amount of salt, −4° C.). A 1:1 mixture of 0.7M sodium hypochlorite in water and saturated NaHCO3 (56 mL total) was added dropwise. The resulting mixture was allowed to stand in the ice bath until layers separated (˜5 minutes). The layers were separated and extracted with DCM (3×30 mL). The organic layer was washed with water (30 mL) and saturated aqueous NaCl (30 mL), then dried over anhydrous Na2SO4, filtered and concentrated to yield (S)-3-formylpyrrolidine-1-carboxylic acid t-butyl ester (3.0 g), which was used without further purification.

1. additionwas added dropwise
2. customseparated (˜5 minutes)
3. customThe layers were separated
4. extractionextracted with DCM (3×30 mL)
5. washThe organic layer was washed with water (30 mL) and saturated aqueous NaCl (30 mL)
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-e7e78588b96f44d3b06bdb972168deaa

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994209B2