Ethanol → Methyl 5-aminobicyclo[3.2.1]octane-1-carboxylate

HRID 1503253Notes

Reaction equation

HRID 1503253 reaction equation
C(OC([NH:11][C:12]12[CH2:19][C:16]([C:20]([O-:22])=[O:21])([CH2:17][CH2:18]1)[CH2:15][CH2:14][CH2:13]2)=O)C1C=CC=CC=1.[CH3:23]CO>[Pd]>[NH2:11][C:12]12[CH2:19][C:16]([C:20]([O:22][CH3:23])=[O:21])([CH2:17][CH2:18]1)[CH2:15][CH2:14][CH2:13]2

Participants

4

Reactant 2

HCID 702EthanolHCID 866683955-(Benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate

Product 1

HCID 68048077Methyl 5-aminobicyclo[3.2.1]octane-1-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate (10 g, 31.5 mmol) in EtOH (50 mL) was added Pd/C (900 mg) under H2 atmosphere at room temperature and stirred overnight. The reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure to afford 5.5 g (96%) of the crude title compound, methyl 5-aminobicyclo[3.2.1]octane-1-carboxylate, as a colorless oil. ESI-MS m/z: 184 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-038829e6a2974898accf3b91e56682c7
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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