3-(1,2,3,4,5,8-Hexahydroindolizin-7-yl)-5-nitro-1H-indole → 3-(Octahydroindolizin-7-yl)-5-amino-1H-indole

HRID 367358Notes

Reaction equation

HRID 367358 reaction equation
[CH2:1]1[CH:9]2[N:4]([CH2:5][CH:6]=[C:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=4)[NH:12][CH:11]=3)[CH2:8]2)[CH2:3][CH2:2]1>C(O)C.O1CCCC1.[Pd]>[CH2:1]1[CH:9]2[N:4]([CH2:5][CH2:6][CH:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=4)[NH:12][CH:11]=3)[CH2:8]2)[CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 153897603-(1,2,3,4,5,8-Hexahydroindolizin-7-yl)-5-nitro-1H-indole

Product 1

HCID 153897613-(Octahydroindolizin-7-yl)-5-amino-1H-indoleYield 85.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 3-(1,2,3,4,5,8-hexahydroindolizin-7-yl)-5-nitro-1H-indole (2.21 g, 6.90 mmol) was dissolved in 95 ml of ethanol and 50 ml of tetrahydrofuran. 5% palladium over carbon was added (550 mg) and the mixture was placed under an atmosphere of hydrogen, at an initial pressure of 60 psi, at room temperature, for 24 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to give 1.51 g of a purple foam. (85%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-7ef4686a526b4daf84bb4739153e9437
Source dataset
uspto-grants-2000_10
Patent number
US06133290

Reaction notes

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