HCID 68819514, compound → 7-(1,1-Dimethylethyl) 2-methyl 3-amino-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylate

HRID 736770Notes

Reaction equation

HRID 736770 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:10]([NH:11]C(C2C=CC=CC=2)C)[CH:9]2[N:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:6]1[CH2:7][CH2:8]2)=[O:4]>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([CH:5]1[CH:10]([NH2:11])[CH:9]2[N:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:6]1[CH2:7][CH2:8]2)=[O:4]

Participants

4

Reactant 1

HCID 68819514HCID 68819514, compound

Product 1

HCID 688178247-(1,1-Dimethylethyl) 2-methyl 3-amino-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylateYield 92.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(1-phenyl-ethylamino)-7-aza-bicyclo[2.2.1]heptane-2,7-dicarboxylic acid 7-tert-butyl ester 2-methyl ester (0.28 g, 0.8 mmol) and 20% palladium hydroxide on carbon (0.2 g) in methanol (5 mL) was stirred under a hydrogen atmosphere (1 atm) for 19 h. The mixture was then filtered through a thin pad of celite and concentrated to provide 3-amino-7-aza-bicyclo[2.2.1]heptane-2,7-dicarboxylic acid 7-tert-butyl ester 2-methyl ester as a colorless oil (0.2 g, 71.4%). MS: 269 (M+H)+.

Workup

  1. filtrationThe mixture was then filtered through a thin pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a0e6dcfcec494325946d622ff0da1785
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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