(1S,2S,5R)-2-(benzylamino-methyl)-7-methyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester → (1S,2S,5R)-2-aminomethyl-7-methyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester

HRID 425798Notes

Reaction equation

HRID 425798 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]2[C@H:10]([CH2:11][CH:12]([CH3:16])[CH2:13]2)[C@H:9]1[CH2:17][NH:18]CC1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]2[C@H:10]([CH2:11][CH:12]([CH3:16])[CH2:13]2)[C@H:9]1[CH2:17][NH2:18])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 66703797(1S,2S,5R)-2-(benzylamino-methyl)-7-methyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester

Product 1

HCID 59411604(1S,2S,5R)-2-aminomethyl-7-methyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (1S,2S,5R)-2-(benzylamino-methyl)-7-methyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester (264 mg) in EtOH (12 mL) was treated with Pd/C 10% (100 mg) and stirred under hydrogen (1 bar) for 16 h. After filtration through celite and removal of the solvents the title compound was obtained as a colourless oil which was used without further purification.

Workup

  1. filtrationAfter filtration
  2. customthrough celite and removal of the solvents the title compound
  3. customwas obtained as a colourless oil which
  4. customwas used without further purification

Sources & evidence

ORD record
ord-fed6148c87b64ddabbb8ec29ee7a8aef
Source dataset
uspto-grants-2012_01
Patent number
US08106215B2

Reaction notes

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