2,3-Dimethyl-1-butene → 2-Isopropyl-2-methyl-1-tosylaziridine

温度

20 °C

To a solution of 2,3-dimethyl butene (300 ml, 2.42 mol) in 7.8 L of dry acetonitrile was added Chloramine-T (749.9 g, 1.1 eq) portionwise over 90 min. The temperature was maintained at approximately 20° C. To this reaction mixture was added phenyltrimethylammonium tribromide (91.4 g, 0.1 eq) in 10 g portions over 90 min. The temperature increased to 26° C. during the addition. The reaction mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated down to approximately 15% of the initial volume and was them filtered, washing the solid with 1 L of acetonitrile. The organic liquid phase was concentrated and the residue dissolved in 2.5 L of EtOAc. The resulting solution was washed twice with water, dried over MgSO4, and concentrated to give a solid. The crude was purified on a large plug of Celite using gradient elution 5% to 25% EtOAc/heptanes to afford 317 g of 2-isopropyl-2-methyl-1-[(4-methylphenyl)sulfonyl]aziridine as a solid.

1. temperatureThe temperature increased to 26° C. during the addition
2. concentrationThe reaction mixture was concentrated down to approximately 15% of the initial volume
3. filtrationfiltered
4. washwashing the solid with 1 L of acetonitrile
5. concentrationThe organic liquid phase was concentrated
6. dissolutionthe residue dissolved in 2.5 L of EtOAc
7. washThe resulting solution was washed twice with water
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customto give a solid
11. customThe crude was purified on a large plug of Celite
12. washelution 5% to 25% EtOAc/heptanes

ORDレコード

ord-9673a0de173b4defac5d009a1703274f

出典データセット

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08188085B2