(1S,3S,5S)-3-(b enzylamino-methyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester → (1S,3S,5S)-tert-Butyl 3-(aminomethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

HRID 2064792Notes

Reaction equation

HRID 2064792 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][NH:15]CC2C=CC=CC=2)[CH2:12][C@H:11]2[C@@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][NH2:15])[CH2:12][C@H:11]2[C@@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67081441(1S,3S,5S)-3-(b enzylamino-methyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Product 1

HCID 58278675(1S,3S,5S)-tert-Butyl 3-(aminomethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A solution of (1S,3S,5S)-3-(b enzylamino-methyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (16.7 mmol) in EtOH (100 mL) is treated with Pd/C (2.0 g, 50% H2O) and stirred under a hydrogen atmosphere (1 bar) for 1 d. An additional amount of Pd/C (2.0 g) is added and the mixture is stirred for further 3 d. After filtration through celite and removal of the solvents the desired amine is obtained which is used without further purification. LC-MS (acidic): tR=0.64 min; [M+H]+=213.3.

Workup

  1. stirringthe mixture is stirred for further 3 d
  2. filtrationAfter filtration
  3. customthrough celite and removal of the solvents the desired amine
  4. customis obtained which
  5. customis used without further purification

Sources & evidence

ORD record
ord-dc5b934b50b7413fb38cb4bca04e79b3
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

Loading…