5-Benzyloxycarbonylamino-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester → Ethyl 5-aminobicyclo[3.2.1]octane-1-carboxylate

HRID 1408855Notes

Reaction equation

HRID 1408855 reaction equation
[CH2:1]([O:3][C:4]([C:6]12[CH2:13][C:10]([NH:14]C(OCC3C=CC=CC=3)=O)([CH2:11][CH2:12]1)[CH2:9][CH2:8][CH2:7]2)=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]12[CH2:13][C:10]([NH2:14])([CH2:11][CH2:12]1)[CH2:9][CH2:8][CH2:7]2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 679813295-Benzyloxycarbonylamino-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester

Product 1

HCID 68048103Ethyl 5-aminobicyclo[3.2.1]octane-1-carboxylateYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Benzyloxycarbonylamino-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester (2.0 g, 6.05 mmol) was dissolved in ethanol (50.0 mL). Pd/C (10%) (0.32 g, 0.30 mmol) was added. The mixture was hydrogenated under 50 psi H2 at rt for 6 hrs. The catalyst was removed by filtration through a layer of Celite®. The filtrate was concentrated under reduced pressure to afford 1.0 g (84%) of the desired product. ESI-MS m/z: 198 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through a layer of Celite®
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ef78f2b07065440ebeed8ffdc85f84f8
Source dataset
uspto-grants-2014_12
Patent number
US08921370B2

Reaction notes

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