Triacetoxyperiodinane → tert-Butyl N-(3-oxopropyl)carbamate

A solution of (3-hydroxypropyl)-carbamic acid tert-butyl ester (0.60 g, 3.4 mmol) in anhydrous CH2Cl2 (17 mL) was treated with Dess-Martin reagent (1.74 g, 4.1 mmol) for 3 hours at room temperature. The reaction mixture was diluted with Et2O (30 mL) and washed with a 20% aqueous solution of sodium thiosulfate (15 mL) followed by a saturated aqueous solution of sodium bicarbonate (15 mL). The combined aqueous phase was then extracted with Et2O (2×35 mL) and re-washed with 20% sodium thiosulfate solution (30 mL), saturated NaHCO3 solution (25 mL), and brine (25 mL). The organic component was then dried (MgSO4), filtered, and concentrated under reduced pressure to provide (3-oxopropyl)-carbamic acid tert-butyl ester as a colorless oil (0.54 g, 91%).

1. washwashed with a 20% aqueous solution of sodium thiosulfate (15 mL)
2. extractionThe combined aqueous phase was then extracted with Et2O (2×35 mL)
3. washre-washed with 20% sodium thiosulfate solution (30 mL), saturated NaHCO3 solution (25 mL), and brine (25 mL)
4. dry with materialThe organic component was then dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure

ORD record

ord-73ab31764ecb43fd8c7ffc2120a2632d

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354934B2