Diisopropylamine → Aziridine, 2-(1,3-benzodioxol-5-yl)-

Temperature

60 °C

A solution of oxime 12 (2.7 g, 15 mmol, 1.0 equiv) in tetrahydrofuran (60 mL) at 25° C. was transferred via cannula to a stirred suspension of lithium aluminum hydride (3.5 g, 61 mmol, 4.0 equiv) and di-iso-propyl amine (8.5 mL, 61 mmol, 4.0 equiv) in tetrahydrofuran (70 mL) at 25° C. The emptied reaction vessel was rinsed with tetrahydrofuran (22 mL) and the resulting solution was also transferred via cannula. The reaction vessel was equipped with a reflux condenser under nitrogen atmosphere and heated to 60° C. via oil bath for 4 h. The mixture was cooled to 25° C., diluted with ice water (400 mL), and the product was extracted with dichloromethane (5×200 mL). The combined organic layers were dried (sodium sulfate), gravity filtered, and concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (5% triethylamine in ethyl acetate) to afford 15 (2.17 g, 88% yield) as a pale yellow oil. Rf=0.40 (5% triethylamine in ethyl acetate); 1H NMR (500 MHz, CDCl3) δ 6.75 (br s, 2H, ArH), 6.70 (br s, 1H, ArH), 5.93 (s, 2H, OCH2O), 2.97 (br s, 1H, ArCH), 2.17 (br s, 1H, CH2), 1.67 (br s, 1H, CH2).

1. customThe emptied reaction vessel
2. washwas rinsed with tetrahydrofuran (22 mL)
3. customThe reaction vessel was equipped with a reflux condenser under nitrogen atmosphere
4. temperatureThe mixture was cooled to 25° C.
5. additiondiluted with ice water (400 mL)
6. extractionthe product was extracted with dichloromethane (5×200 mL)
7. dry with materialThe combined organic layers were dried (sodium sulfate), gravity
8. filtrationfiltered
9. concentrationconcentrated by rotary evaporation
10. customThe residue was purified by silica gel column chromatography (5% triethylamine in ethyl acetate)

ORD record

ord-0aa8f3350af341c8beab5a24ae5cdd1e

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466142B2