(5-Benzylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(4-methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone → (hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(4-methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone

HRID 244034Notes

Reaction equation

HRID 244034 reaction equation
C([N:8]1[CH2:12][CH:11]2[CH2:13][N:14]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=3[N:26]3[N:30]=[CH:29][CH:28]=[N:27]3)=[O:17])[CH2:15][CH:10]2[CH2:9]1)C1C=CC=CC=1>CCO.CC(O)=O.[OH-].[OH-].[Pd+2]>[CH2:13]1[CH:11]2[CH2:12][NH:8][CH2:9][CH:10]2[CH2:15][N:14]1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=1[N:26]1[N:27]=[CH:28][CH:29]=[N:30]1)=[O:17]

Participants

5

Reactant 1

HCID 67116518(5-Benzylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(4-methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone

Product 1

HCID 67116159(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(4-methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

(5-Benzylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(4-methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone in EtOH (20 mL) and AcOH (1 mL) was continuously flowed through a 20 wt % Pd(OH)2/C cartridge at a rate of 1 mL/min for 2 h at 50° C. and 50 bar using a H-cube apparatus. Then the reaction was concentrated and neutralized with 5% Na2CO3 (aq), and extracted with CH2Cl2 (3×). Combined organics and dried (Na2SO4) to give (hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(4-methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone as a clear oil that was used without further purification. 1H NMR (CDCl3): 7.83-7.80 (m, 2H), 7.50 (d, J=2.5 Hz, 1H), 7.32 (d, J=8.5 Hz, 1H), 6.96 (dd, J=8.5, 2.5 Hz, 1H), 3.89 (s, 3H), 3.75-3.63 (m, 2H), 3.27 (s, 1H), 3.08 (dd, J=11.9, 8.1 Hz, 1H), 2.94 (dt, J=11.4, 5.7 Hz, 2H), 2.88-2.75 (m, 2H), 2.69 (dd, J=17.8, 14.3 Hz, 1H), 2.56 (dd, J=11.4, 3.9 Hz, 1H).

Workup

  1. concentrationThen the reaction was concentrated
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialCombined organics and dried (Na2SO4)

Sources & evidence

ORD record
ord-b3b6f8f93c184cb5b42cefe7fe64cb7f
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

Loading…