Water → (+/-)-cis-5,6,7a,8,9,10,11, 11a-octahydro-4H-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline

Temperature

0 °C

5,6,8,9,10,11-Hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (2.84 g, 11.4 mmol) was dissolved in TFA (35 mL). The reaction was cooled to 0° C. NaCNBH3(2.15 g, 34.27 mmol) was added in small portions over 30 min, keeping the temperature less than 5° C. The reaction was stirred at 0° C. for 2 h. Ice was added to the reaction flask, and the reaction was basified with 50% NaOH until pH=14. Water (20 mL) was added to dissolve the precipitate. The reaction was extracted with CHCl3(3×20 mL). The combined organic layers were washed with brine, dried, and concentrated to afford the title compound (1.67 g, 68%) as a pale-brown, amorphous solid. 1H NMR (CDCl3, 300 MHz) δ 6.80–7.00 (m, 2H), 6.55–6.6.70 (m, 1H), 3.20–3.40 (m, 2H), 2.95–3.20 (m, 2H), 2.75–2.95 (m, 2H), 2.50–2.75 (m, 4H), 2.00–2.20 (m, 2H), 1.85–2.00 (m, 1H), 1.70–1.85 (m, 1H) ppm.

1. customthe temperature less than 5° C
2. additionIce was added to the reaction flask
3. dissolutionto dissolve the precipitate
4. extractionThe reaction was extracted with CHCl3(3×20 mL)
5. washThe combined organic layers were washed with brine
6. customdried
7. concentrationconcentrated

ORD record

ord-ad93a196bbba455eba00aba647b9d54a

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07081455B2