Ethyl ketone → HCID 18187644, Verbindung

Temperatur

0 °C

A solution of diisopropylamine (0.63 mL, 4.5 mmol) in THF (16 mL) at 0° C. was treated with 1.6 M n-butyllithium in sol'n in hexanes (2.8 mL). The resulting solution was stirred at 0° C. for 10 min, then cooled to −78° C. 3-Pentanone (0.41 mL, 4.1 mmol) was added and the resulting mixture was stirred cold for 1 h. A solution of 1-(t-butoxycarbonyl)4-formylpiperidine (435 mg, 2.05 mmol) (from Step B) in THF (3 mL) was then added. After 15 min, the reaction was quenched with sat'd ammonium chloride (25 mL) and extracted with ether (100 mL). The extract was dried over magnesium sulfate and concentrated. MPLC (Biotage) on a 40S silica cartridge using 4:1 v/v, then 3:2 v/v hexanes/ethyl acetate as the eluent afforded 517 mg (85%) of the title compound.

1. temperaturecooled to −78° C
2. stirringthe resulting mixture was stirred cold for 1 h
3. waitAfter 15 min
4. customthe reaction was quenched with sat'd ammonium chloride (25 mL)
5. extractionextracted with ether (100 mL)
6. dry with materialThe extract was dried over magnesium sulfate
7. concentrationconcentrated

ORD-Eintrag

ord-11527d422a4d45aaa28b357d1922d772

Quelldatensatz

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06593346B2