Dibenzyl 1,3-dioxo-4-phenyl-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-9-yl phosphate → 1,3-Dioxo-4-phenyl-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-9-yl dihydrogen phosphate

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Reaction Steps

A solution of the dibenzyl phosphate (336) (100 mg, 0.17 mmol) prepared as described in example 447 in methanol/tetrahydrofuran (3:1, 70 mL) was hydrogenated at 60 psi over Pd-C (5%, catalytic) with stirring for 3 hours. The reaction mixture was then filtered through celite and concentrated in vacuo. Trituration from ethyl acetate/hexane gave the phosphate (337) (49 mg, 71%) as a yellow solid, mp 285–295° C. 1H NMR δ [(CD3)2SO] 12.01 (br s, 1H), 11.09 (br s, 1H), 8.66 (br s, 1H), 7.63 (m, 3H), 7.57 (br d, J=8.6 Hz, 1H), 7.50–7.44 (m, 4H). Found: C, 55.19; H, 3.29; N, 6.34; P, 6.84. C20H13N2O6P.1/2H2O requires: C, 55.18; H, 3.71; N, 6.43; P, 7.12.

Provenance & Evidence