3-Azido-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester → Ethyl 3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 897259Notes

Reaction equation

HRID 897259 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([N:14]=[N+]=[N-])[CH2:10]2)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([NH2:14])[CH2:10]2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 583468423-Azido-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester

Product 1

HCID 18507024Ethyl 3-amino-8-azabicyclo[3.2.1]octane-8-carboxylateYield 68.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-azido-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester (1.42 g, 6.28 mmol) in methanol (62 mL) was added Pd (10% weight on carbon, 100 mg). The mixture was degassed and charged with hydrogen (g) 3×, and stirred for 12 hrs. The mixture was filtered through celite and concentrated. The crude residue was purified by flash chromatography (gradient elution: 0→20% MeOH/dichloromethane) to provide 855 mg of a clear oil (68%, 3 steps). 1H NMR (300 MHz, CDCl3) □ ppm 1.26 (t, J=7.1 Hz, 3H), 1.66 (m, 4H), 1.83 (m, 2H), 1.95 (m, 2H), 3.16 (m, 1H), 4.13 (q, J=7.1 Hz, 2H), 4.27 (m, 2H); MS (ESI+Q1MS) m/z 199 [M+H]+

Workup

  1. customThe mixture was degassed
  2. additioncharged with hydrogen (g) 3×
  3. filtrationThe mixture was filtered through celite
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography (gradient elution: 0→20% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-ad3d6198d4704bcbaabaa692eb00d1e4
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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