Dimethyl Sulfoxide → tert-Butyl N-(3-oxopropyl)carbamate

Temperature

-40 °C

A solution of oxalyl chloride (0.27 ml, 3.15 mmole) in dry dichloromethane (8 ml) was cooled to −78° C. Dimethyl sulfoxide (0.45 ml, 6.29 mmole) in dichloromethane (1 ml) was added dropwise maintaining the reaction temperature at −40° C. The reaction mixture was stirred for 5 minutes and a solution of (3-hydroxy-propyl)-carbamic acid tert-butyl ester (0.50 g, 2.86 mmole) in dichloromethane (3 ml) was added dropwise. After stirring for 15 minutes, triethylamine (1.99 ml, 14.3 mmole) was added and the mixture allowed to warm to ambient temperature. The reaction was quenched by adding water (10 ml), extracted with dichloromethane and the organic extracts were washed with aqueous hydrochloric acid solution (2M), saturated sodium bicarbonate solution and water. The organic layer was dried under magnesium sulfate and the solvent removed in vacuo to afford the title compound (0.45 g). 1H NMR (CDCl3) δ 9.81 (1H, s), 3.45-3.40 (2H, t, J=5 Hz), 2.72-2.69 (2H, t, J=5 Hz), 1.43 (9H, s).

1. stirringAfter stirring for 15 minutes
2. temperatureto warm to ambient temperature
3. customThe reaction was quenched
4. additionby adding water (10 ml)
5. extractionextracted with dichloromethane
6. washthe organic extracts were washed with aqueous hydrochloric acid solution (2M), saturated sodium bicarbonate solution and water
7. customThe organic layer was dried under magnesium sulfate
8. customthe solvent removed in vacuo

ORD record

ord-5e33892f80b14714906f32e61d90335b

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07348339B2