Benzene, 1-bromo-3-(trifluoromethyl)- → HCID 66997470, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylcarbamate from Example 252 Step B (50.3 mg, 0.222 mmol), tris(dibenzylidineacetone)dipalladium(0) (4.07 mg, 4.45 μmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (8.30 mg, 0.013 mmol), potassium phosphate, tribasic (54.2 mg, 0.311 mmol) and 1-bromo-3-(trifluoromethyl)benzene (0.032 mL, 0.233 mmol) were combined in toluene (2 mL) and put under nitrogen. The reaction mixture was heated at 80° C. overnight. The reaction was quenched with water (1 mL), the phases were separated, and the organic phase was applied to a 4 g silica gel cartridge and purified using a gradient of 1-20% ethyl acetate/hexanes over 15 minutes to give tert-butyl(3aR,4S,6aS)-2-(3-(trifluoromethyl)phenyl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate: 1H NMR (400 MHz, pyridine-d5) δ ppm 7.73 (d, J=6.3, 1H), 7.33 (t, J=7.8, 1H), 7.06 (d, J=7.4, 1H), 6.91 (s, 1H), 6.76 (d, J=7.9, 1H), 4.13-4.02 (m, 1H), 3.44 (d, J=10.0, 1H), 3.34-3.27 (m, 1H), 3.21-3.12 (m, 1H), 2.99 (d, J=10.1, 1H), 2.81-2.70 (m, 2H), 2.12 (td, J=12.6, 6.4, 1H), 2.06-1.95 (m, 1H), 1.73 (dq, J=15.0, 7.5, 1H), 1.55 (s, 9H), 1.44-1.34 (m, 1H); MS (ESI+) m/z 371 (M+H)+.

Provenance & Evidence