[H-].[Na+].[NH:3]1[C:7]2=[C:8]3[C:13](=[CH:14][CH:15]=[C:6]2[CH:5]=[CH:4]1)[N:12]=[CH:11][CH:10]=[CH:9]3.[CH2:16]1[O:19][C@@H:17]1[CH3:18].[Cl-].[NH4+]>C1COCC1>[N:3]1([CH2:16][C@H:17]([OH:19])[CH3:18])[C:7]2=[C:8]3[C:13](=[CH:14][CH:15]=[C:6]2[CH:5]=[CH:4]1)[N:12]=[CH:11][CH:10]=[CH:9]3
A mixture of sodium hydride, 60% dispersion in mineral oil, (0.76 g, 18.5 mmol) and THF (30 mL) was cooled to 0° C. under Ar. A mixture of 1H-pyrrolo[2,3-f]quinoline (G. Bartoli, G. Palmieri, M. Bosco and R. Dalpozzo, Tetrahedron Letts., 1989, 30, 2129-2132) (2.5 g, 14.8 mmol) and THF (20 mL) was added and the mixture was left at 0° C. for 1 h. (R)-propylene oxide (2.1 mL, 30 mmol) was added and the mixture was left at room temperature for 48 h. Saturated ammonium chloride solution (100 mL) was added and the mixture was extracted with Et2O (3×100 mL), the extracts were combined, washed with brine (2×100 mL), dried (MgSO4), concentrated in vacuo and purified by column chromatography [SiO2; Et2O] to give the product (0.61 g, 18% yield) as a pale yellow oil: IRνmax(Nujol)/cm−1 3106, 1361, 1117, 826, 805, and 731; NMR δH (400 MHz, CDCl3) 1.35 (3H, d, J 6.5 Hz), 2.76 (1H, br), 4.33 (1H, m), 4.44 (1H, m), 4.56 (I1H, m), 6.64 (1H, d, J 3.0 Hz), 7.20 (1H, d, J 3.0 Hz), 7.30 (1H, dd, J8.5 and 4.5 Hz), 7.71 (1H, d, J 9.0 Hz), 7.87 (1H, d, J 9.0 Hz), 8.52 (1H, d, J 8.5 Hz) and 8.67 (1H, m).
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