Diisopropylamine → HCID 13590114, compound

Temperature

-78 °C

n-Butyllithium in hexane (4.10 mmol) is added by syringe to a solution of diisopropylamine (4.10 mmol) in anhydrous tetrahydrofuran (16 ml) at -78° C. The resulting solution is stirred at -78° C. for 15 min. prior to the addition of a solution of 1-(t-butyldimethylsilyl)-4-(1,1-dimethyl-prop-2-enyl)-azetidin-2-one 3 (2.0 mmol) in anhydrous tetrahydro uran (2 ml). After an additional 15 min. at -78° C., the reaction mixture is added via a Teflon tube to a mixture of N-acetylimidazole (4.1 mmol) in anhydrous tetrahydrofuran (16 ml) at -78° C. The resulting yellow reaction mixture is stirred at -78° C. for 15 min., then quenched by addition of saturated aqueous ammonium chloride solution (10 ml). The reaction mixutre is diluted with ether (100 ml) and washed with 2.5N hydrochloric acid solution (25 ml) water (25 ml) and brine. The organic phase is dried over magnesium sulfate and concentrated in vacuo to yield crude products. This material is chromatographed on silica gel (2:1 petroleum ether:ether) to yield 4.

1. waitAfter an additional 15 min. at -78° C.
2. stirringThe resulting yellow reaction mixture is stirred at -78° C. for 15 min.
3. customquenched by addition of saturated aqueous ammonium chloride solution (10 ml)
4. additionThe reaction mixutre is diluted with ether (100 ml)
5. washwashed with 2.5N hydrochloric acid solution (25 ml) water (25 ml) and brine
6. dry with materialThe organic phase is dried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. customto yield crude products
9. customThis material is chromatographed on silica gel (2:1 petroleum ether:ether)
10. customto yield 4

ORD record

ord-271817b7d478489790fde7de65697910

Source dataset

uspto-grants-1986_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04582643