Tetrahydrofuran → methyl 1-{1-[2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl]piperidin-4-yl}-1H-indole-6-carboxylate

온도

40 °C

2.92 g of methyl 1-piperidin-4-yl-1H-indole-6-carboxylate hydrochloride and 2.92 g of (7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)acetaldehyde were added with 58.4 mL of tetrahydrofuran and 14.6 mL of acetic acid warmed to 40° C. and the reaction mixture was stirred for about 3 hours. The reaction mixture was cooled with an ice-water bath, and 2.52 g of sodium triacetoxyborohydride was added portionwise divided into three. The reaction mixture was warmed to room temperature and 30 minutes later, progress of the reaction was confirmed. The reaction mixture was cooled with an ice-water bath again and 87 mL of toluene and 29 mL of water were added thereto and the aqueous layer was discarded. The organic layer was washed with 49 mL, 69 mL, 30 mL of 1 N aqueous sodium hydroxide sequentially and then with 29 mL, 14 mL of 5% sodium chloride solution and 14 mL of water. The solvent was evaporated and 4.80 g of the crude title compound was obtained.

1. temperatureThe reaction mixture was cooled with an ice-water bath
2. temperatureThe reaction mixture was warmed to room temperature and 30 minutes later
3. temperatureThe reaction mixture was cooled with an ice-water bath again
4. washThe organic layer was washed with 49 mL, 69 mL, 30 mL of 1 N aqueous sodium hydroxide sequentially
5. customThe solvent was evaporated

ORD 기록

ord-5633f7b5a04e47b28610fabd2a9c1869

출처 데이터셋

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08110688B2