Water → tert-Butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate

HRID 712455Notes

Reaction equation

HRID 712455 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C:2]=12.O>COCCO.[Pd]>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]2[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][CH:2]12

Participants

5

Reactant 2

HCID 962WaterHCID 68201977tert-Butyl 5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate

Product 1

HCID 68729079tert-Butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylateYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of tert-butyl 5H-pyrrolo[3,4-b]pyridine-6(7H)-carboxylate (1.50 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. The resulted mixture was cooled to rt, poured into 100 mL of water and 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 pale yellow oil (0.95 g, 65.00%). 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: 227.2 (M+1).

Workup

  1. temperatureThe resulted mixture was cooled to rt
  2. extractionextracted 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-65be96303e40409b9b3ef7c6f2abece2
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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