Water → 6-Ethyloctahydro-1H-pyrrolo[3,4-b]pyridine

HRID 712463Notes

Reaction equation

HRID 712463 reaction equation
[CH2:1]([N:3]1[CH2:11][C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1)[CH3:2].O>COCCO.[Pd]>[CH2:1]([N:3]1[CH2:11][CH:10]2[CH:5]([NH:6][CH2:7][CH2:8][CH2:9]2)[CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 67976988HCID 67976988, compound

Product 1

HCID 545798326-Ethyloctahydro-1H-pyrrolo[3,4-b]pyridineYield 72.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-ethyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine (2.00 g) in glycol monomethyl ether was added a catalytic amount of 10% Pd/C. The suspension was heated to 70° C. and stirred for 6 h under H2 (2 MPa), then cooled to rt, and poured into 100 mL of water. The mixture was extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the title compound as yellow oil (1.50 g, 70.00%). The crude product was used for the next step without further purification. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 155.0 (M+1).

Workup

  1. temperaturecooled to rt
  2. extractionThe mixture was extracted with CH2Cl2 (50 mL×3)
  3. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4c88d0ed22c84a1fbf16cdd4e424e671
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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