2-Azabicyclo(2.2.1)hept-5-en-3-one → (1S,4R)-Methyl 4-aminocyclopent-2-enecarboxylate hydrochloride

Temperature

5 °C

20.0 g (183.3 mmol) of 2-azabicyclo[2.2.1]hept-5-en-3-one and 400 mL (400 mmol) of a 1N-hydrogen chloride methanol solution were put into a four-necked flask (500 mL volume) equipped with a thermometer, and the mixture was heated and refluxed for 10 hours. The obtained reaction mixture was concentrated under reduced pressure. The residue was dissolved in 27 mL of diethyl ether, and then cooled to 5° C. The precipitated crystals were filtered off using a glass filter. The obtained crystals were dried under reduced pressure to give 25.6 g (144.1 mmol) of cis-4-amino-2-cyclopentene-1-carboxylic acid methyl ester hydrochloride. The yield was 78.6%.

1. custom(500 mL volume) equipped with a thermometer
2. temperaturethe mixture was heated
3. temperaturerefluxed for 10 hours
4. customThe obtained reaction mixture
5. concentrationwas concentrated under reduced pressure
6. dissolutionThe residue was dissolved in 27 mL of diethyl ether
7. filtrationThe precipitated crystals were filtered off
8. filtrationfilter
9. customThe obtained crystals were dried under reduced pressure

ORD record

ord-3b7681c4aeac46b99c1a1556cbef4367

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07038059B2