Hydrochloric Acid → HCID 96398683, compound

HRID 1004624Notes

Reaction equation

HRID 1004624 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:12][CH:11]2[CH:7]([N:8](C(C3C=CC=CC=3)C)[CH2:9][CH2:10]2)[CH2:6]1)=[O:4].C([O-])=O.[NH4+].Cl>CO.[Pd]>[CH3:1][O:2][C:3]([N:5]1[CH2:12][C@@H:11]2[C@@H:7]([NH:8][CH2:9][CH2:10]2)[CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723923Ammonium formateHCID 54183072HCID 54183072, compound

Product 1

HCID 96398683HCID 96398683, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (1 g) was added to a solution of 1-(1-phenyl-ethyl)-hexahydro-pyrrolo[3,4-b]pyrrole-5-carboxylic acid methyl ester (Diastereomer B, 4.9 g, 17.9 mmol), ammonium formate (5.6 g, 89 mmol) and 5N hydrochloric acid (4.0 ml, 20 mmol) in methanol (180 ml) at room temperature under nitrogen. The mixture was stirred and heated at reflux for 1 hour. Upon cooling the catalyst was removed by filtration through celite (washing with methanol). The filtrate was evaporated and the residue was partitioned between dichloromethane and saturated aqueous potassium carbonate. The aqueous layer was further extracted with dichloromethane (×1) and n-butanol (×1). The combined extracts were evaporated, and the residue was purified by chromatography on silica gel eluting with CH2Cl2 /MeOH/NH3 (80:8:1) to give the title amine (2.7 g, 89%) as a pale yellow oil; δ (360 MHz, d6 -DMSO) 1.50-1.58 (1H, m), 1.76-1.86 (1H, m), 2.66 (1H, br s), 2.76-2.88 (2H, m), 3.04-3.08 (1H, m), 3.10 (1H, br s, NH), 3.18 (1H, dd, J=11.4, 2.5 Hz), 3.40-3.52 (2H, m), 3.56 (3H, s, CO2Me), 3.66 (1H, br s).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. temperatureUpon cooling the catalyst
  4. customwas removed by filtration through celite (washing with methanol)
  5. customThe filtrate was evaporated
  6. customthe residue was partitioned between dichloromethane and saturated aqueous potassium carbonate
  7. extractionThe aqueous layer was further extracted with dichloromethane (×1) and n-butanol (×1)
  8. customThe combined extracts were evaporated
  9. customthe residue was purified by chromatography on silica gel eluting with CH2Cl2 /MeOH/NH3 (80:8:1)

Sources & evidence

ORD record
ord-83cc2d72f65849659043b1e86e0234b0
Source dataset
uspto-grants-2000_04
Patent number
US06051591

Reaction notes

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