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

HRID 1266056Notes

Reaction equation

[CH:1]1[C:10]2[C:11]3[CH2:16][NH:15][CH2:14][CH2:13][C:12]=3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][CH:2]=1.[BH3-]C#N.[Na+].[OH-].[Na+].O>C(O)(C(F)(F)F)=O>[CH:1]1[C:10]2[C@H:11]3[CH2:16][NH:15][CH2:14][CH2:13][C@H:12]3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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) δ6.80-7.00 (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.

Workup

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

Sources & evidence

ORD record: ord-7c1e5ddfc17c4acb8030b3384db49820
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548493B1

Reaction notes

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