9-Nitro-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline hydrochloride → (+)-1,2,3,5,6,10b-Hexahydropyrrolo[2,1-a]isoquinolin-9-amine hydrochloride

HRID 369973Notes

Reaction equation

HRID 369973 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]3[CH2:17][CH2:16][CH2:15][CH:12]32)=[CH:7][CH:6]=1)([O-])=O>C(O)C.[Pd]>[ClH:1].[CH2:15]1[CH:12]2[C:13]3[C:8]([CH2:9][CH2:10][N:11]2[CH2:17][CH2:16]1)=[CH:7][CH:6]=[C:5]([NH2:2])[CH:14]=3

Participants

4

Reactant 1

HCID 215842749-Nitro-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline hydrochloride

Product 1

HCID 21584345(+)-1,2,3,5,6,10b-Hexahydropyrrolo[2,1-a]isoquinolin-9-amine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension (+)-9-nitro-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline hydrochloride (1.83 g, 7.18 mmol) and 10% Pd-C (0.2 g) in ethanol (150 ml) was hydrogenated at 50 psi for 0.75 h. The solution was filtered and the filtrate was concentrated to a volume of 25 ml. It was then heated to reflux to dissolve all of the solid and upon cooling the product precipitated. The title compound was isolated as a white solid (1.37 g, 85%), m.p. 239-41.5° C.; [α]D +62.5° (c 1.13, MeOH). This salt was a single enantiomer by chiral CE.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated to a volume of 25 ml
  3. temperatureIt was then heated
  4. temperatureto reflux
  5. dissolutionto dissolve all of the solid
  6. temperatureupon cooling the product
  7. customprecipitated

Sources & evidence

ORD record
ord-e4f937878fdc4a79b5fa25188c76f8f2
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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