Benzyl Isothiocyanate → HCID 10138216, compound

HRID 1244450Notes

Reaction equation

HRID 1244450 reaction equation
[CH2:1]([N:8]=[C:9]=[S:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([C@@H:20]3[C:32]4[NH:31][C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]=4[CH2:23][CH2:22][NH:21]3)=[CH:19][C:14]=2[O:13][CH2:12]1.[K+].[Br-]>>[CH2:1]([NH:8][C:9]([N:21]1[CH2:22][CH2:23][C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:31][C:32]=2[C@H:20]1[C:18]1[CH:17]=[CH:16][C:15]2[O:11][CH2:12][O:13][C:14]=2[CH:19]=1)=[S:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 2346Benzyl IsothiocyanateHCID 253877Potassium BromideHCID 746214HCID 746214, compound

Product 1

HCID 10138216HCID 10138216, compoundYield 80%

Procedure

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.

Workup

  1. customprovided Example 2b in 80% yield

Sources & evidence

ORD record
ord-e0e0653ff9414ff0b2a3716753c2a917
Source dataset
uspto-grants-2006_10
Patent number
US07122554B2

Reaction notes

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