Benzyl 5-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate → 1-(2,5-diazabicyclo[2.2.1]hept-2-yl)-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone

HRID 2173358Notes

Reaction equation

HRID 2173358 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13]([N:15]3[CH2:20][CH:19]4[CH2:21][CH:16]3[CH2:17][N:18]4C(OCC3C=CC=CC=3)=O)=[O:14])=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1>[Pd].CO>[CH:16]12[CH2:21][CH:19]([NH:18][CH2:17]1)[CH2:20][N:15]2[C:13](=[O:14])[CH2:12][C:9]1[CH:8]=[CH:7][C:6]([N:1]2[CH:5]=[N:4][N:3]=[N:2]2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 67518237Benzyl 5-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 675179311-(2,5-diazabicyclo[2.2.1]hept-2-yl)-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 5-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (517 mg, 1.24 mmol) and palladium on carbon (131 mg) in methanol (50 mL) were stirred under a hydrogen atmosphere (balloon) for overnight. The reaction mixture was filtered and concentrated to afford 1-(2,5-diazabicyclo[2.2.1]hept-2-yl)-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone. LC/MS: [(M+1)]+=285.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a55da58eb5cd4fac82c86c3acd18a0c1
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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