Methanol → (1S,4R)-Methyl 4-aminocyclopent-2-enecarboxylate hydrochloride

Temperature

0 °C

(−)-2-Azabicyclo[2,2,1]hept-5-en-3-one (20.00 g, 0.1833 mmol) was dissolved in MeOH (140 mL) and this mixture was cooled to 0° C. Thionyl chloride (29.4 mL, 0.403 mol) was then added dropwise, keeping the temperature less than 15° C. Upon completion of addition, the mixture was left to stir at 5° C. for 2 hours. The solvent was removed under reduced pressure to yield an oil, which was dried further under high vacuum overnight at 35° C. to afford the title compound as a white solid (33 g) which was used without further purification. 1H NMR (300 MHz, DMSO, δ): 8.45 (s, 3H), 6.03 (m, 1H), 5.87 (m, 1H), 4.13 (m, 1H), 3.60 (m, 4H), 2.53 (m, 1H) and 1.89 (m, 1H).

1. customthe temperature less than 15° C
2. additionUpon completion of addition
3. waitthe mixture was left
4. customThe solvent was removed under reduced pressure
5. customto yield an oil, which
6. customwas dried further under high vacuum overnight at 35° C.

ORD record

ord-c6782d4b8f394e058ffcbdafb53f55bc

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933225B2