Water → Hexahydro-2-(phenylmethyl)-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione

HRID 712466Notes

Reaction equation

HRID 712466 reaction equation
[CH2:1]([N:8]1[C:16](=[O:17])[C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>COCCO.[Pd]>[CH2:1]([N:8]1[C:16](=[O:17])[CH:15]2[CH:10]([CH2:11][NH:12][CH2:13][CH2:14]2)[C:9]1=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 711901HCID 711901, compound

Product 1

HCID 22646963Hexahydro-2-(phenylmethyl)-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dioneYield 61.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 2-benzyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione (3.50 g) in glycol monomethyl ether was added a catalytic amount of 10% Pd/C. The suspension was heated to 35° C. and stirred for 6 h under H2, then cooled to rt, poured into 100 mL of water and extracted with CH2Cl2 (70 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 (2.20 g, 60%). 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: 245.2 (M+1).

Workup

  1. temperaturecooled to rt
  2. extractionextracted with CH2Cl2 (70 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-15a8107a0aed42029b5d2c0dccb14121
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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