Benzyl Isothiocyanate → HCID 10138216, compound

Participants

Reaction Steps

Addition of benzyl isothiocyanate to (1R)-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline (1R isomer of compound (III)) provided Example 2b in 80% yield: mp 205–207° C. H1 NMR (DMSO-d6) δ: 11.0 (s, 1H), 8.5 (t, J=5 Hz, 1H), 7.8 (s, 1H), 7.6 (s, 1H), 7.43 (d, J=7 Hz, 1H), 7.4–7.28 (m, 8H), 6.85 (dd, J=1.4, 8 Hz, 1H), 6.69 (d, J=8 Hz, 1H), 5.88 (s, 2H), 4.88 (overlapping dd, J=4.7, 14 Hz, 2H), 4.11 (dd, J=4.4, 14 Hz, 1H), 3.51–3.44 (m, 1H), 2.94–2.84 (m, 1H), 2.78 (dd, J=4, 15 Hz, 1H); MS ES+m/e 442 (p+1), ES−m/e 440 (p−1); IR (KBr, cm−1): 1518, 1503, 1487; Elemental analysis: Anal. Calcd for C26H23N3O2S: C, 70.72; H, 5.25; N, 9.51. Found: C, 70.30; H, 5.27; N, 9.42; 74% ee.

Provenance & Evidence