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

温度

0 °C

A solution of (S)-3-hydroxymethylpyrrolidine-1-carboxylic acid t-butyl ester (25.0 g, 124 mmol) in DCM (200 mL) was cooled with stirring to 0° C. A solution of potassium bromide (1.5 g, 12.4 mmol) and sodium bicarbonate (1.5 g, 17.4 mmol) dissolved in water (100 mL) was added. After 15 minutes of stirring at 0° C. 2,2,6,6,-tetramethylpiperidin-1-oxyl (195.3 mg, 1.2 mmol) was added, followed by the slow addition of sodium hypochlorite (77.3 mL, 136.6 mmol) dropwise keeping the internal temperature in the 6-8° C. range. The mixture was placed in an ice bath until the layers separated and the layers were back extracted with DCM (200 mL). The combined organic layers were washed with 1M NaCl in water (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. extractionthe layers were back extracted with DCM (200 mL)
7. washThe combined organic layers were washed with 1M NaCl in water (200 mL)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated

ORDレコード

ord-eca74d1ed5dd40cab4626e43ddbe3fd6

出典データセット

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08853255B2