1-(4-Benzylamino-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester → Tert-butyl 1-(4-aminophenyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate

HRID 1400022Notes

Reaction equation

HRID 1400022 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]3[CH:19]=[CH:18][C:17]([NH:20]CC4C=CC=CC=4)=[CH:16][CH:15]=3)([CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)([CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 675083621-(4-Benzylamino-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

Product 1

HCID 67509408Tert-butyl 1-(4-aminophenyl)-3-azabicyclo[3.1.0]hexane-3-carboxylateYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(4-benzylamino-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (3.0 g, 8.2 mmol) in methanol (20 mL) was added 10% Pd/C (600 mg, 20% by weight). Flask was evacuated and hydrogen was introduced. The reaction mixture was stirred under hydrogen and progress of the reaction was monitored by TLC. On completion, the reaction mixture was filtered through celite pad using methanol as solvent. The filtrate was evaporated to provide the title compound (2.2 g, 97%) as brown solid and subjected to further reaction without any purification.

Workup

  1. customFlask was evacuated
  2. additionhydrogen was introduced
  3. filtrationOn completion, the reaction mixture was filtered through celite pad
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-3a07dac2c0f640319f730401d71d3177
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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