Trifluoroacetic acid → 3-(1-Cyclopentyl-octahydro-pyrrolo[3,2-b]pyrrol-3-yl)-6-fluoro-1H-indole

A solution containing 36 (2.0 g, 4.8 mmol) in DCM (20 mL) was cooled to 0° C. TFA (6 mL) was added and the pink reaction mixture was stirred at 0° C. After 1 h, the reaction mixture was warmed to ambient temperature then concentrated in vacuo. The residue was dissolved in EtOAc and the organic solution was washed successively with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 1.4 g of 37 which was used without further purification. 1H NMR (CDCl3, 300 MHz): δ8.50 (br s, 1H), 7.58 (dd, J=5.4, 8.4 Hz, 1H), 7.05-7.01 (m, 2H), 6.92-6.85 (m, 1H), 4.17-4.11 (m, 1H), 3.92 (app q, J=6.0 Hz, 1H), 3.74 (app q, J=6.6 Hz, 1H), 3.21-3.15 (m, 1H), 3.08-2.88 (m, 3H), 2.75-2.67 (m, 2H), 1.96-1.78 (m, 5H), 1.61 (m, 4H) ppm. Mass spectrum, m/z [314.2] (M+H)+.

1. temperaturethe reaction mixture was warmed to ambient temperature
2. concentrationthen concentrated in vacuo
3. dissolutionThe residue was dissolved in EtOAc
4. washthe organic solution was washed successively with saturated aqueous NaHCO3 and brine
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-e0bd399feedb429fac2c5c6b5200e27c

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399683B2