Methanol → 2',3'-Dihydro-1'H-spiro[cyclopropane-1,4'-isoquinoline]

Temperature

0 °C

0.5 g (2.7 mmol) 1′H-spiro[cyclopropane-1,4′-isoquinoline]-1′,3′(2′H)-dione in 50 mL THF were heated to the reflux temperature of the solvent. 11 mL (11 mmol) of a 1M borane in THF solution were added dropwise and the mixture was refluxed for 3 h. The reaction mixture was cooled to 0° C. and mixed with 50 mL methanol. The reaction mixture was evaporated down, the residue was combined with 15 mL of a 4M hydrochloric acid solution and refluxed for 30 min. After neutralisation with 15 mL of an aqueous 4M sodium hydroxide solution the mixture was extracted twice with ethyl acetate. The combined organic phases were dried and evaporated down. The product was purified by HPLC. The product-containing fractions were combined and evaporated down.

1. temperaturethe mixture was refluxed for 3 h
2. customThe reaction mixture was evaporated down
3. temperaturerefluxed for 30 min
4. extractionAfter neutralisation with 15 mL of an aqueous 4M sodium hydroxide solution the mixture was extracted twice with ethyl acetate
5. customThe combined organic phases were dried
6. customevaporated down
7. customThe product was purified by HPLC
8. customevaporated down

ORD record

ord-820b14ef8ef045398b4eb69d4d0c7738

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829006B2