Hydrochloric Acid → HCID 70664474, compound

Temperature

100 °C

cis-Ethyl 6-chloro-3a-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-benzo[e]isoindole-2(9bH)-carboxylate (0.162 mmol, 50 mg) was dissolved in dichloromethane (1 ml). Iodotrimethylsilane (0.487 mmol, 0.070 ml, 98 mg) was added and the reaction mixture was heated to 100° C. for 30 minutes in the microwave. 2 N HCl in MeOH (2 ml) was added to the reaction mixture was stirred at rt for 20 minutes. The reaction mixture was then concentrated in vacuo and the residue was dissolved in 2 N HCl and washed with ether. The acidic extract was basified using 4 N NaOH and extracted with ether. The ether extract was then dried over magnesium sulphate, filtered and concentrated in vacuo to give a crude residue that was purified by basic prep-HPLC. The purified fractions were concentrated in vacuo and then redissolved in 2 N HCl in MeOH and concentrated in vacuo to give cis-6-chloro-3a-methyl-2,3,3a,4-tetrahydro-1H-benzo[e]isoindol-5(9bH)-one hydrochloride (2.4 mg), m/z=236.3 [M+H]+.

1. concentrationThe reaction mixture was then concentrated in vacuo
2. dissolutionthe residue was dissolved in 2 N HCl
3. washwashed with ether
4. extractionThe acidic extract
5. extractionextracted with ether
6. extractionThe ether extract
7. dry with materialwas then dried over magnesium sulphate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give a crude residue that
11. customwas purified by basic prep-HPLC
12. concentrationThe purified fractions were concentrated in vacuo
13. dissolutionredissolved in 2 N HCl in MeOH
14. concentrationconcentrated in vacuo

ORD record

ord-23a1f36ec73d4dac93573090fd050739

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729274B2