Sodium borohydride → HCID 59408994, compound

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Reaction Steps

To a room temperature stirred solution of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-oxo-propionitrile (1.0 g, 4.5 mmol) in anhydrous N,N-dimethylformamide (20 ml) was added excess sodium borohydride in small portions over 3 days. After 5 days the mixture was quenched with 1M hydrochloric acid (50 ml) and extracted with ethyl acetate (3×100 ml). The organic layer was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue obtained was purified by flash column chromatography (SiO2, 20% EtOAc in hexanes) to afford (E)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-acrylonitrile as an off white solid (348 mg). 400 MHz 1H NMR (CDCl3) δ: 7.55 (d, J=8.0 Hz, 1H), 7.5 (d, J=16.4 Hz, 1H), 7.3 (s, 1H), 7.18 (t, J=7.6 Hz, 1H), 7.03 (dd, J=0.8 and 6.8 Hz, 1H), 5.7 (d, J=16.4 Hz, 1H), 4.17 (t, J=5.6 Hz, 2H), 3.0 (t, J=6.4 Hz, 2H), 2.28-2.22 (m, 2H); LCMS: 208 [M+].

Provenance & Evidence