Methyl iodide → HCID 14698663, compound

Temperature

50 °C

Distilled diisopropylamine (1.98 g, 19.6 mmol) was added to dry tetrahydrofuran (10 ml) under anhydrous conditions. To the stirred solution at 0° C. was added 1.55M n-butyllithium (12.6 ml, 19.6 mmol) in hexane dropwise. After 15 minutes a solution of the compound (1a) (2.2 g, 7.8 mmole) in tetrahydrofuran (10 ml) was added dropwise at 0° C. The reaction mixture was stirred for 1 hour at ambient temperature 30 minutes at 50° C. and then cooled to 0° C. Methyl iodide (2.78 g, 19.6 mmol) was added dropwise, and the reaction mixture stirred at ambient temperature for about 16 hours. The reaction was quenched with saturated ammonium chloride (20 ml) and acidified with 3N hydrochloric acid. The reaction mixture was extracted with diethyl ether (3×100 ml), the extracts combined, washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated in vacuo to give a tan solid. This compound was chromatographed on a 5×15 cm column of silica gel eluted with 5 percent isopropanol/hexane to yield the desired product as a solid, m.p. 78-80° C.

1. temperaturecooled to 0° C
2. stirringthe reaction mixture stirred at ambient temperature for about 16 hours
3. customThe reaction was quenched with saturated ammonium chloride (20 ml)
4. extractionThe reaction mixture was extracted with diethyl ether (3×100 ml)
5. washwashed with saturated aqueous sodium chloride
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. customto give a tan solid
9. customThis compound was chromatographed on a 5×15 cm column of silica gel
10. washeluted with 5 percent isopropanol/hexane

ORD record

ord-898c7739eb9b4ac2b775d22b22850e1b

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04876366