Carbonic acid, bis(1,1-dimethylethyl) ester → tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate

HRID 1793642Notes

Reaction equation

HRID 1793642 reaction equation
Cl.[CH:2]12[NH:9][CH:6]([CH2:7][CH2:8]1)[CH2:5][C:4](=[O:10])[CH2:3]2.[C:11]([O:15][C:16](=O)[O:17]C(C)(C)C)([CH3:14])([CH3:13])[CH3:12]>CCO>[C:11]([O:15][C:16]([N:9]1[CH:6]2[CH2:7][CH2:8][CH:2]1[CH2:3][C:4](=[O:10])[CH2:5]2)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 130912188-Azabicyclo[3.2.1]octan-3-one hydrochloride

Product 1

HCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 8-aza-bicyclo[3.2.1]octan-3-one hydrochloride (4.5 g, 0.028 mol) in 100 mL of EtOH was added carbonic acid di-tert-butyl ester (12 g, 2 eq.) and 11 mL of TEA. The resulting mixture was heated at 60° C. for 3 h. The volatile fraction was removed and the residue was partitioned between EtOAc and water. The EtOAc layer was washed with saturated sodium chloride, dried over Na2SO4 and concentrated. Silica gel column purification with 20% EtOAc in hexane gave 3-oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (6.25 g).

Workup

  1. customThe volatile fraction was removed
  2. customthe residue was partitioned between EtOAc and water
  3. washThe EtOAc layer was washed with saturated sodium chloride
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customSilica gel column purification with 20% EtOAc in hexane

Sources & evidence

ORD record
ord-55b815432aad4d159e753de12c860ab4
Source dataset
uspto-grants-2006_07
Patent number
US07081531B2

Reaction notes

Loading…