Pyridine → (+-)-1-(tert-Butoxycarbonyl)pyrrolidine-3-carboxaldehyde

To a solution of pyridine (9.5 g, 0.12 mol) in dichloromethane (150 mL) was added chromium trioxide (6.0 g, 0.06 mol). The internal reaction temperature was not allowed to exceed 20° C. during the addition. After 15 minutes, the stirred mixture was charged with a solution of tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (2.0 g, 10 mmol) in dichloromethane (30 mL). After 15 minutes, the solution was decanted from the reaction vessel which was washed with dichloromethane (200 mL). The organics were combined, washed with 5% aqueous sodium hydroxide (3×100 mL), then washed with 5% hydrochloric acid (100 mL), then washed with 5% aqueous sodium bicarbonate (100 mL), and finally washed with 5% aqueous sodium chloride (100 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford tert-butyl 3-formylpyrrolidine-1-carboxylate that was used without additional purification.

1. additionto exceed 20° C. during the addition
2. waitAfter 15 minutes
3. customthe solution was decanted from the reaction vessel which
4. washwas washed with dichloromethane (200 mL)
5. washwashed with 5% aqueous sodium hydroxide (3×100 mL)
6. washwashed with 5% hydrochloric acid (100 mL)
7. washwashed with 5% aqueous sodium bicarbonate (100 mL)
8. washfinally washed with 5% aqueous sodium chloride (100 mL)
9. dry with materialThe organics were dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-c9eb831ad1504dbf8ff82468b344d09c

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455477B2