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

HRID 11158Notes

Reaction equation

HRID 11158 reaction equation
[P:1]([O:19][C:20]1[CH:32]=[CH:31][C:30]2[NH:29][C:28]3[CH:27]=[C:26]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:25]4[C:39](=[O:43])[NH:40][C:41](=[O:42])[C:24]=4[C:23]=3[C:22]=2[CH:21]=1)([O:11]CC1C=CC=CC=1)([O:3]CC1C=CC=CC=1)=[O:2]>CO.O1CCCC1.[Pd]>[P:1]([OH:3])([OH:11])([O:19][C:20]1[CH:32]=[CH:31][C:30]2[NH:29][C:28]3[CH:27]=[C:26]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:25]4[C:39](=[O:43])[NH:40][C:41](=[O:42])[C:24]=4[C:23]=3[C:22]=2[CH:21]=1)=[O:2]

Participants

4

Reactant 1

HCID 21980748Dibenzyl 1,3-dioxo-4-phenyl-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-9-yl phosphate

Product 1

HCID 219804661,3-Dioxo-4-phenyl-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-9-yl dihydrogen phosphateYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

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.

Workup

  1. filtrationThe reaction mixture was then filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50297983814043f68e5ed0382c170795
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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