HCID 10184680, compound → HCID 10132705, compound

HRID 1815217Notes

Reaction equation

HRID 1815217 reaction equation
[O:1]=[C:2]1[C@H:18]2[N:6]([C@H:7]([CH2:19][CH2:20][CH2:21][NH:22]C(=O)OCC3C=CC=CC=3)[C:8]3[NH:9][C:10]4[C:15]([C:16]=3[CH2:17]2)=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:5](=[O:33])[C@@H:4]2[CH2:34][CH2:35][CH2:36][N:3]12>CO.[Pd]>[NH2:22][CH2:21][CH2:20][CH2:19][C@@H:7]1[C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH2:17][C@H:18]2[C:2](=[O:1])[N:3]4[CH2:36][CH2:35][CH2:34][C@H:4]4[C:5](=[O:33])[N:6]12)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

4

Reactant 1

HCID 10184680HCID 10184680, compound

Product 1

HCID 10132705HCID 10132705, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The solution of benzyl 3-[(5aS,12R,14aS)-5,14-dioxo-2,3,5a,6,11,12,14,14a-octahydro-1H,5H-pyrrolo[1″,2″:4′,5′]pyrazino[2′,1′:6,1]pyrido[3,4-b]indol-12-yl]propylcarbamate (0.1 mmol) in methanol (2.0 ml) was stirred under hydrogen (1.5 atm) in the presence of 5% Palladium on carbon for 1 hour. The solid was removed by filtration, and the solution was evaporated to afford (5aS,12R,14aS)-12-(3-aminopropyl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1″,2″:4′,5′]pyrazino[2′,1′:6,1]pyrido[3,4-b]indole-5,14-dione (95%). The (5aS,12S,14aS)-12-(3-aminopropyl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1″,2″:4′,5′]pyrazino[2′,1′:6,1]pyrido[3,4-b]indole-5,14-dione was prepared in a similar manner, but using 3-[(5aS,12S,14aS)-5,14-dioxo-2,3,5a,6,11,12,14,14a-octahydro-1H,5H-pyrrolo[1″,2″:4′,5′]pyrazino[2′,1′:6,1]pyrido [3,4-b]indol-12-yl]propylcarbamate as starting material. ESIMS (MH+): 29a, 353.2; 29b, 353.2.

Workup

  1. customThe solid was removed by filtration
  2. customthe solution was evaporated

Sources & evidence

ORD record
ord-9e90096b1d0147b99a850b7cce827572
Source dataset
uspto-grants-2005_04
Patent number
US06878737B2

Reaction notes

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