Hydrochloric Acid → Ethyl 1-(2-Aminoethyl)-5,5-dimethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride

HRID 1024048Notes

Reaction equation

HRID 1024048 reaction equation
[C:1]([CH2:3][N:4]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]2[CH2:14][C:15]([CH3:18])([CH3:17])[CH2:16][C:5]1=2)#[N:2].[ClH:19].C(OCC)(=O)C>[Pd].C(O)C>[ClH:19].[NH2:2][CH2:1][CH2:3][N:4]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]2[CH2:14][C:15]([CH3:17])([CH3:18])[CH2:16][C:5]1=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 68208418HCID 68208418, compound

Product 1

HCID 86661242Ethyl 1-(2-Aminoethyl)-5,5-dimethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 500-mL Parr reactor bottle was purged with nitrogen and charged with 10% palladium on carbon (50% wet, 2.0 g dry weight), 110c (4.5 g, 18 mmol), 12% hydrochloric acid (9.2 mL, 37 mmol), ethyl acetate (80 mL) and ethanol (52 mL). The bottle was attached to a Parr hydrogenator, evacuated, charged with hydrogen gas to a pressure of 50 psi and shaken for 6 h. After this time, the hydrogen was evacuated, and nitrogen was charged into the bottle. Celite 521 (10.0 g) was added, and the mixture was filtered through a pad of Celite 521. The filter cake was washed with ethanol (2×50 mL), and the combined filtrates were concentrated to dryness under reduced pressure. The crude residue 110d was carried onto the next step without further purification.

Workup

  1. customA 500-mL Parr reactor bottle was purged with nitrogen
  2. customevacuated
  3. additioncharged with hydrogen gas to a pressure of 50 psi
  4. customAfter this time, the hydrogen was evacuated
  5. additionnitrogen was charged into the bottle
  6. additionCelite 521 (10.0 g) was added
  7. filtrationthe mixture was filtered through a pad of Celite 521
  8. washThe filter cake was washed with ethanol (2×50 mL)
  9. concentrationthe combined filtrates were concentrated to dryness under reduced pressure
  10. customThe crude residue 110d was carried onto the next step without further purification

Sources & evidence

ORD record
ord-ada886ccdc2141c68cf4edcaae0dc80c
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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