[3-Methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-carbamic acid benzyl ester → 3-Methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butylamine

HRID 1009304Notes

Reaction equation

HRID 1009304 reaction equation
C(OC(=O)[NH:10][CH:11]([C:16]12[O:23][CH2:22][C:19]([CH3:24])([CH2:20][O:21]1)[CH2:18][O:17]2)[CH2:12][CH:13]([CH3:15])[CH3:14])C1C=CC=CC=1>CCO.[Pd]>[CH3:14][CH:13]([CH3:15])[CH2:12][CH:11]([NH2:10])[C:16]12[O:17][CH2:18][C:19]([CH3:24])([CH2:20][O:21]1)[CH2:22][O:23]2

Participants

4

Reactant 1

HCID 67298262[3-Methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-carbamic acid benzyl ester

Product 1

HCID 574469573-Methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To [3-methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-carbamic acid benzyl ester (3.2 g, 9.2 mmol) in absolute EtOH (30 mL) was added 10% Pd in activated carbon (320 mg, 10%) under nitrogen. The reaction mixture was hydrogenated at 50 psi for 6 h. The reaction was monitored by TLC and the reaction mixture was filtered through Celite. The solvent was removed to get 3-methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butylamine as a white solid.

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-f56ac762d7fa40549833960e457bff63
Source dataset
uspto-grants-2011_07
Patent number
US07973037B2

Reaction notes

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