Ammonia → {(3S)-3-(3,4-Dichlorophenyl)-1-[6-(dimethylamino)-2-pyridinyl]-6-oxopiperidinyl}acetaldehyde Hydrochloride

温度

140 °C

Copper (I) iodide (6.4 g, 33.3 mmol), potassium carbonate (6.3 g, 45.4 mmol) and 6-bromo-2-(dimethylamino)pyridine (WO 9843971) (9 g, 45.4 mmol) were added consecutively to a solution of (5S)-5-(3,4-dichlorophenyl)-5-(1,3-dioxolan-2-ylmethyl)-2-piperidinone (WO 9807722) (10 g, 30.3 mmol), in 1-methyl-2-pyrrolidinone (50 ml), and the mixture was stirred at 140° C. for 4 hours. The cooled mixture was poured into 4N hydrochloric acid, then carefully basified using 10% aqueous ammonia. The aqueous mixture was extracted with ethyl acetate (3×200 ml), and the combined organic extracts were washed with brine, dried (MgSO4) and evaporated under reduced pressure to give an orange oil. The crude product was purified by column chromatography on silica gel using methanol:dichloromethane (5:95) as eluant, and repeated using ethyl acetate as eluant. The product was treated with 1N ethereal hydrochloric acid, and evaporated under reduced pressure to afford the title compound.

1. extractionThe aqueous mixture was extracted with ethyl acetate (3×200 ml)
2. washthe combined organic extracts were washed with brine
3. dry with materialdried (MgSO4)
4. customevaporated under reduced pressure
5. customto give an orange oil
6. customThe crude product was purified by column chromatography on silica gel
7. additionThe product was treated with 1N ethereal hydrochloric acid
8. customevaporated under reduced pressure

ORDレコード

ord-21c838b827c04abdbed331dd02a294dc

出典データセット

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07060836B2