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

Temperature

0 °C

A solution of (S)-3-hydroxymethyl-pyrrolidine-1-carboxylic acid t-butyl ester (25.0 g, 124 mmol, 1.0 eq.) in DCM (200 mL) was cooled with stirring to 0° C. A solution of potassium bromide (1.5 g, 12.4 mmol, 0.1 eq.) and sodium bicarbonate (1.5 g, 17.4 mmol, 0.14 eq.) dissolved in water (100 mL) was added. After 15 minutes of stirring at 0° C., TEMPO (195.3 mg, 1.2 mmol, 0.01 eq.) was added, followed by the slow addition of sodium hypochlorite (77.3 mL, 136.6 mmol, 1.1 eq.) dropwise keeping the internal temperature in the 6-8° C. range. The mixture was placed in an ice bath until the layers separated. The organic layer was separated and the aqueous layer was extracted with DCM (200 mL). The combined organic layers were washed with saturated aqueous NaCl (200 mL), dried over Na2SO4, filtered, and concentrated to yield crude (S)-3-formylpyrrolidine-1-carboxylic acid t-butyl ester (21.5 g).

1. additionwas added
2. stirringAfter 15 minutes of stirring at 0° C.
3. customin the 6-8° C. range
4. customThe mixture was placed in an ice bath until the layers
5. customseparated
6. customThe organic layer was separated
7. extractionthe aqueous layer was extracted with DCM (200 mL)
8. washThe combined organic layers were washed with saturated aqueous NaCl (200 mL)
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-f3716d2532e440d4933975481d7b0d37

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969403B2