4-Methylmorpholine → HCID 178523777, compound

To a stirred, ice-cold solution of the product from part (a) (1.70 g, 6.13 mmole) in dry methylene chloride (30 ml) were added sequentially, 1-hydroxybenzotriazole (0.92 g, 6.77 mmole), 5-indanol (2.0 g, 15 mmole), N-methylmorpholine (0.80 g, 7.92 mmole) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.53 g, 7.98 mmole). After 10 minutes, the resulting solution was concentrated to an oil which was stirred at room temperature for 18 hours and then dissolved in methylene chloride (150 ml). The latter solution was washed in turn with water (2×50 ml), saturated aqueous sodium bicarbonate solution (2×25 ml), 2N hydrochloric acid (2×25 ml) and saturated brine (2×25 ml), then dried over anhydrous magnesium sulphate and filtered. Evaporation of the solvent under vacuum, gave an oil which was purified by chromatography on silica gel eluting with hexane-ethyl acetate (4:1). The appropriate fractions were combined and the solvent evaporated under vacuum to furnish the title compound as a white solid (2.20 g, 91%), which was crystallised from a mixture of diethyl ether and n-pentane, m.p. 68°-69° C. Found: C,73.30; H,7.04; N,3.43. C24H27NO4 requires C,73.26; H,6.92; N,3.56%.

1. concentrationthe resulting solution was concentrated to an oil which
2. dissolutiondissolved in methylene chloride (150 ml)
3. washThe latter solution was washed in turn with water (2×50 ml), saturated aqueous sodium bicarbonate solution (2×25 ml), 2N hydrochloric acid (2×25 ml) and saturated brine (2×25 ml)
4. dry with materialdried over anhydrous magnesium sulphate
5. filtrationfiltered
6. customEvaporation of the solvent under vacuum
7. customgave an oil which
8. customwas purified by chromatography on silica gel eluting with hexane-ethyl acetate (4:1)
9. customthe solvent evaporated under vacuum

ORD record

ord-f4d8cb4d133f45b08aafe9c18a01b04c

Source dataset

uspto-grants-1991_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05030654