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

HRID 1411487Notes

Reaction equation

HRID 1411487 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), 107c (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 ethyl 1-(2-aminoethyl)-5,5-dimethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride 107d 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. additionwas 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 ethyl 1-(2-aminoethyl)-5,5-dimethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride 107d was carried onto the next step without further purification

Sources & evidence

ORD record
ord-1609f84449564ae8a81024da12182f50
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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