(1R,3S,4S)-3-(benzylamino-methyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester → tert-butyl (1R,3S,4S)-3-(aminomethyl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

HRID 882795Notes

Reaction equation

HRID 882795 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][NH:15]CC2C=CC=CC=2)[C@@H:12]2[CH2:23][C@H:9]1[CH2:10][CH2:11]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])[C@@H:12]2[CH2:23][C@H:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 66865917(1R,3S,4S)-3-(benzylamino-methyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Product 1

HCID 66866957tert-butyl (1R,3S,4S)-3-(aminomethyl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A solution of (1R,3S,4S)-3-(benzylamino-methyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (39.8 mmol) in EtOH (120 mL) is treated with Pd/C (10%, 4.0 g) and stirred under a hydrogen atmosphere (7 bar) for 1 d. An additional amount of Pd/C (1.0 g) is added and the mixture is stirred for further 6 h under a hydrogen atmosphere (7 bar). After filtration through celite and removal of the solvents in vacuo the desired amine is obtained which is used without further purification. LC-MS (basic): tR=0.85 min; [M+H]+=227.3.

Workup

  1. stirringthe mixture is stirred for further 6 h under a hydrogen atmosphere (7 bar)
  2. filtrationAfter filtration
  3. customthrough celite and removal of the solvents in vacuo the desired amine
  4. customis obtained which
  5. customis used without further purification

Sources & evidence

ORD record
ord-11205cd6a04f4a65b28cc3f5567ee946
Source dataset
uspto-grants-2012_08
Patent number
US08236801B2

Reaction notes

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