3-Tolylboronic acid → (4As)-10-(2-fluorophenyl)-1,2,3,4,4a,5-hexahydropyrazino[1,2-a][1,5]benzodiazepin-6(7h)-one

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Reaction Steps

(4aS)-3-Benzyl-10-(2-fluorophenyl)-1,2,3,4,4a,5-hexahydropyrazino[1,2-a][1,5]benzodiazepin-6(7H)-one was prepared according to the procedure outlined in Example 89 substituting 2-fluorophenylboronic acid for 3-methylphenylboronic acid and Example 116B for Example 4. The intermediate (4aS)-3-benzyl-10-(2-fluorophenyl)-1,2,3,4,4a,5-hexahydropyrazino[1,2-a][1,5]benzodiazepin-6(7H)-one was purified via HPLC, and underwent benzyl removal in ethanol (20 mL) with Pd(OH)2—C (20%, 1 wet, 76 mg, 1.250 mmol) which was stirred for 2 hours under H2 (30 psi) at room temperature. The catalyst was removed by filtration. HPLC purification afforded the title compound. as the trifluoroacetic acid salt. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.50-7.56 (m, 1H), 7.36-7.43 (m, 1H), 7.20-7.30 (m, 4H), 7.07 (d, J=8.24 Hz, 1H), 3.57-3.63 (m, 1H), 3.31-3.40 (m, 4H), 2.95-3.07 (m, 2H), 2.70 (dd, J=13.58, 7.17 Hz, 1H), 2.07 (d, J=12.51 Hz, 1H); MS (DCI+) m/z 312 (M+H)+.

Provenance & Evidence