Iodoethane → HCID 15128680, Verbindung

Temperatur

-78 °C

To a freshly prepared solution of lithium diisopropylamide in tetrahydrofuran (6 equivalents; prepared by addition of 19.2 ml of a 2.6M solution of n-butyllithium in hexane to 15 ml of freshly distilled diisopropylamine in 80 ml of tetrahydrofuran) at -78° C., was added 3.0 g (8.35 mmole) of 7-chloro-1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one (see Example 1C . After stirring at -78° C. for 1.5 hours, 3 ml of hexamethylphosphoric triamide was added along with 13.6 ml of iodoethane (filtered through alumina to remove iodine). The mixture was stirred at -78° C. for 30 minutes (under argon), and then at -20° C. (dry-ice/carbon tetrachloride bath) for six days. The reaction was quenched with 1N hydrochloric acid (50 ml), and the aqueous layer was extracted with ethyl acetate (three times). The ethyl acetate extracts and the tetrahydrofuran were combined, washed with saturated sodium bicarbonate and saturated sodium chloride, and dried (magnesium sulfate). The solution was concentrated, combined with 0.31 g of previously prepared crude product and flash chromatographed (silica gel/3:1-hexane:ethyl acetate) yielding 0.61 g of product.

1. stirringThe mixture was stirred at -78° C. for 30 minutes (under argon)
2. customThe reaction was quenched with 1N hydrochloric acid (50 ml)
3. extractionthe aqueous layer was extracted with ethyl acetate (three times)
4. washwashed with saturated sodium bicarbonate and saturated sodium chloride
5. dry with materialdried (magnesium sulfate)
6. concentrationThe solution was concentrated
7. customof previously prepared crude product and flash
8. customchromatographed (silica gel/3:1-hexane:ethyl acetate)

ORD-Eintrag

ord-ef2f98eaa704433298f15a3ed1736cee

Quelldatensatz

uspto-grants-1988_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04752645