Formaldehyde → Methyl 4-cyclobutyl-2-methyl-5-(6-methyl-1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepin-2-yl)benzoate

온도

40 °C

Into a 100-mL round-bottom flask, was placed a mixture of methyl 4-cyclobutyl-5-(1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepin-2-yl)-2-methylbenzoate hydrochloride (compound 82.7, 40 mg, 0.11 mmol), NaBH(OAc)3 (75 mg, 0.35 mmol), and formaldehyde (37 wt %) (26 μL, 0.33 mmol) in tetrahydrofuran (4 mL). The resulting mixture was stirred for 2 h at 40° C., then cooled and the pH of the solution was adjusted to 8-9 with sodium bicarbonate (sat.). The aqueous phase was extracted with ethyl acetate (2×20 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to yield 20 mg (crude) of the title compound as a yellow solid.

1. customInto a 100-mL round-bottom flask, was placed
2. temperaturecooled
3. extractionThe aqueous phase was extracted with ethyl acetate (2×20 mL)
4. dry with materialthe combined organic layers were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure

ORD 기록

ord-f19a4ce641de436ca5cd4856f67c95cc

출처 데이터셋

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09428502B2