4-Chlorostyrene → (7r,11s)-5-[2-(4-Chlorophenyl)ethyl]-2-methyl-6,7,8,9,10,11-hexahydro-5h-7,11-epiminocycloocta[b]indole

HRID 2176126Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH2:11][CH:12]3[NH:17][CH:16]([C:5]2=1)[CH2:15][CH2:14][CH2:13]3.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[CH2:26])=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][N:7]2[C:8]3[C:4](=[CH:3][C:2]([CH3:1])=[CH:10][CH:9]=3)[C:5]3[C@H:16]4[NH:17][C@@H:12]([CH2:11][C:6]2=3)[CH2:13][CH2:14][CH2:15]4)=[CH:21][CH:20]=1

Participants

Reactant 2

HCID 140854-Chlorostyrene

HCID 67545475HCID 67545475, compound

Product 1

HCID 67544811(7r,11s)-5-[2-(4-Chlorophenyl)ethyl]-2-methyl-6,7,8,9,10,11-hexahydro-5h-7,11-epiminocycloocta[b]indole

Procedure

The coupling of 2-methyl-6,7,8,9,10,11-hexahydro-5H-7,11-epiminocycloocta[b]indole (226 mg, 1.0 mmol; Example 118A) and 1-chloro-4-vinylbenzene (277 mg, 1.99 mmol; Aldrich) was performed according to the procedure described in Example 114B to afford the title compound as a racemic mixture. Individual enantiomers were obtained by preparative chiral supercritical fluid chromatography (ChiralPak® OD-H 5 μm column, 21×250 mm, 35° C., 10-50% gradient of CH3OH—CO2 containing 0.1% diethylamine, 20 minutes) to afford the title compound as the first-eluting enantiomer: 1H NMR (300 MHz, methanol-d4) δ ppm 1.03-1.17 (m, 1H), 1.28-1.43 (m, 2H), 1.65 (d, J=13 Hz, 1H), 1.76-1.94 (m, 2H), 1.98 (d, J=17 Hz, 1H), 2.40 (s, 3H), 2.90 (dd, J=17, 8 Hz, 1H), 2.97-3.15 (m, 2H), 3.47-3.54 (m, 1H), 4.15-4.27 (m, 1H), 4.31-4.44 (m, 2H), 6.93-6.99 (m, 2H), 7.15 (s, 1H), 7.18 (d, J=8 Hz, 2H), 7.26 (d, J=8 Hz, 1H); MS (DCI/NH3) m/z 365 367 (M+H)+.

Sources & evidence

ORD record: ord-5091685a27fd424abea3ff22adad4fe7
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09063126B2

Reaction notes

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